Middletown to Boston (BOS) flights from $294.50 round trip, Nov 2026–Feb 2027
Axel-exclusive from $294.50 round trip (Mon Jan 4–Tue Jan 5, 2027, American nonstop), published Oct 29, 2026; one-way from $156.75 (Mon Jan 4, American nonstop). 90 departure dates priced, one adult, economy.
Compare flight prices from Middletown to Boston for your dates. There are no recent complete one-adult round trips here to set a price target.
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Middletown to Boston flight prices at a glance
- One-way: from $156.75 (American, nonstop) on Mon, Jan 4, 2027; one-way totals sit beside each departure in the calendar.
- Cheapest day to leave: Sunday departures had the lowest published round trips (median $310); Wednesday the highest (median $325).
Middletown to Boston flight prices on popular dates
Exact date pairs with their published Axel-exclusive totals: the coming weekends, the holiday weeks and the cheapest week of each month. One adult, economy, USD, including required taxes. Open a pair for its flights; the full calendar below has every priced date.
| Depart | Return | Nights | Airline | Axel-exclusive total | Why this pair |
|---|---|---|---|---|---|
| Sat, Nov 14, 2026 | Mon, Nov 16, 2026 | 2 | American, nonstop | $310 | Weekend of Sat, Nov 14 |
| Sat, Nov 14, 2026 | Fri, Nov 20, 2026 | 6 | American, nonstop | $310 | Cheapest week in Nov 2026 |
| Sat, Nov 21, 2026 | Mon, Nov 23, 2026 | 2 | American, nonstop | $310 | Weekend of Sat, Nov 21 |
| Sat, Nov 21, 2026 | Tue, Dec 1, 2026 | 10 | American, nonstop | $310 | Thanksgiving week |
| Tue, Dec 1, 2026 | Mon, Dec 7, 2026 | 6 | American, nonstop | $310 | Cheapest week in Dec 2026 |
| Thu, Dec 3, 2026 | Sun, Dec 6, 2026 | 3 | American, nonstop | $310 | Weekend of Sat, Dec 5 |
| Sat, Dec 5, 2026 | Mon, Dec 7, 2026 | 2 | American, nonstop | $310 | Weekend of Sat, Dec 5 |
| Sat, Dec 12, 2026 | Mon, Dec 14, 2026 | 2 | American, nonstop | $310 | Weekend of Sat, Dec 12 |
| Sat, Dec 19, 2026 | Mon, Dec 21, 2026 | 2 | American, nonstop | $387.50 | Weekend of Sat, Dec 19 |
| Fri, Dec 25, 2026 | Mon, Jan 4, 2027 | 10 | American, nonstop | $341 | Christmas week |
| Fri, Jan 1, 2027 | Mon, Jan 4, 2027 | 3 | American, nonstop | $330.15 | Weekend of Sat, Jan 2 |
| Mon, Jan 4, 2027 | Sun, Jan 10, 2027 | 6 | American, nonstop | $294.50 | Cheapest week in Jan 2027 |
Middletown to Boston one-way flight prices
Cheapest one-way: $156.75 on Mon, Jan 4, 2027, American, nonstop. One-way totals run $156.75 to $234 across 90 departure dates; each departure in the calendar below lists its one-way price beside the round trips. Published Oct 29, 2026.
Middletown to Boston round trip flight prices and average fare
Published round trips start at $294.50 and run to $376.65 for the lowest fare on each of 90 departure dates; the median lowest round trip is $310, and 62 of the 90 dates have a round trip at $310 or less. One adult, economy, Axel-exclusive totals including required taxes. Published Oct 29, 2026.
Cheapest day of week and month to fly Middletown to Boston
Cheapest month by published price: January 2027, where the lowest round trip per departure date has a median of $294.50; dearest: December 2026 at $325. Cheapest day of the week to leave: Sunday (median lowest round trip $310); dearest: Wednesday ($325). Published Oct 29, 2026.
Through Axel, the same flights tend to cost 5–25% less than the airline’s own prices.
Middletown (MDT) to Boston (BOS): round-trip and one-way prices for 90 departure dates, Nov 14, 2026–Feb 11, 2027. One adult, economy. Open a departure for return options; use the chooser below for other travelers and cabins.
American, nonstop, from $294.50 round trip · American, out: 1 stop via PHL, back: nonstop, from $308.75 round trip
Saved nonstop flight times: 1h 37m outbound; 1h 42m returning.
How to read the calendar: published Axel-exclusive USD totals for one adult, including required taxes; basic economy may apply. Each return range includes its own prices. Only the listed dates and options are priced. Date links open published details; live search checks availability and lets you select flights.
Hotels: under a trip, hotels in Boston for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.
Middletown to Boston flight prices by month
November 2026: Nov 14–17 from $310 · Nov 18 from $325 · Nov 19–23 from $310 · Nov 24 from $356.50 · Nov 25 from $376 · Nov 26–30 from $356.50.
December 2026: Dec 1 from $310 · Dec 2 from $325 · Dec 3–8 from $310 · Dec 9 from $325 · Dec 10–15 from $310 · Dec 16 from $325 · Dec 17 from $310 · Dec 18 from $337.90 · Dec 19–20 from $376.65 · Dec 21–22 from $341 · Dec 23 from $359.75 · Dec 24–29 from $341 · Dec 30 from $359.75 · Dec 31 from $341.
January 2027: Jan 1–3 from $330.15 · Jan 4–5 from $294.50 · Jan 6 from $308.75 · Jan 7–12 from $294.50 · Jan 13 from $308.75 · Jan 14–19 from $294.50 · Jan 20 from $308.75 · Jan 21–26 from $294.50 · Jan 27 from $308.75 · Jan 28–31 from $294.50.
February 2027: Feb 1–2 from $294.50 · Feb 3 from $308.75 · Feb 4–9 from $294.50 · Feb 10 from $308.75 · Feb 11 from $294.50.
Month summaries show the lowest displayed round-trip total for each departure. Match your return date to the calendar below.
Middletown to Boston flights in November 2026: price by departure date
MDT → BOS · USD · 1 adult · economy · published Oct 29, 2026
Sat, Nov 14, 2026 · round trip · return Nov 15–23: American $310, nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD; return Nov 24–28: American $356.50, nonstop / United $408.25, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $165, nonstop
Hotels in Boston for these nights (Nov 14–15, 2026 · 1 night · 2 adults, 1 room): 3★ Fairfield Inn & Suites Boston Cambridge, $207 total · 4★ Hilton Boston Park Plaza Hotel, $233 total · 5★ Omni Boston Hotel at the Seaport, $285 total
Sun, Nov 15, 2026 · round trip · return Nov 16–23: American $310, nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD; return Nov 24–29: American $356.50, nonstop / United $408.25, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $165, nonstop
Hotels in Boston for these nights (Nov 15–16, 2026 · 1 night · 2 adults, 1 room): 3★ Fairfield Inn & Suites Boston Cambridge, $203 total · 4★ Hilton Boston Park Plaza Hotel, $200 total · 5★ The Liberty, a Marriott Luxury Collection Hotel, Boston, $357 total
Mon, Nov 16, 2026 · round trip · return Nov 17–23: American $310, nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD; return Nov 24–30: American $356.50, nonstop / United $408.25, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $165, nonstop
Hotels in Boston for these nights (Nov 16–17, 2026 · 1 night · 2 adults, 1 room): 3★ The Inn at Longwood Medical, $286 total · 4★ The Whitney Hotel, $674 total · 5★ The Ritz-Carlton, Boston, $553 total
Tue, Nov 17, 2026 · round trip · return Nov 18–23: American $310, nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD; return Nov 24–30: American $356.50, nonstop / United $408.25, out: 1 stop via IAD, back: 1 stop via IAD; return Dec 1: American $310, nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $165, nonstop
Hotels in Boston for these nights (Nov 17–18, 2026 · 1 night · 2 adults, 1 room): 3★ The Inn at Longwood Medical, $286 total · 4★ The Colonnade Hotel Back Bay, $550 total · 5★ The Liberty, a Marriott Luxury Collection Hotel, Boston, $820 total
Wed, Nov 18, 2026 · round trip · return Nov 19–23: American $325, out: 1 stop via PHL, back: nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD; return Nov 24–30: American $371.50, out: 1 stop via PHL, back: nonstop / United $408.25, out: 1 stop via IAD, back: 1 stop via IAD; return Dec 1–2: American $325, out: 1 stop via PHL, back: nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $180, out: 1 stop via PHL
Hotels in Boston for these nights (Nov 18–19, 2026 · 1 night · 2 adults, 1 room): 3★ The Inn at Longwood Medical, $337 total · 4★ Hilton Boston Park Plaza Hotel, $421 total · 5★ The Liberty, a Marriott Luxury Collection Hotel, Boston, $734 total
Thu, Nov 19, 2026 · round trip · return Nov 20–23: American $310, nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD; return Nov 24–30: American $356.50, nonstop / United $408.25, out: 1 stop via IAD, back: 1 stop via IAD; return Dec 1–3: American $310, nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $165, nonstop
Hotels in Boston for these nights (Nov 19–20, 2026 · 1 night · 2 adults, 1 room): 3★ Fairfield Inn & Suites Boston Cambridge, $157 total · 4★ YOTEL Boston, $210 total · 5★ Omni Boston Hotel at the Seaport, $301 total
Fri, Nov 20, 2026 · round trip · return Nov 21–23: American $310, nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD; return Nov 24–30: American $356.50, nonstop / United $408.25, out: 1 stop via IAD, back: 1 stop via IAD; return Dec 1–4: American $310, nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $165, nonstop
Hotels in Boston for these nights (Nov 20–21, 2026 · 1 night · 2 adults, 1 room): 3★ Fairfield Inn & Suites Boston Cambridge, $154 total · 4★ Hilton Boston Park Plaza Hotel, $173 total · 5★ Omni Boston Hotel at the Seaport, $256 total
Sat, Nov 21, 2026 · round trip · return Nov 22–23: American $310, nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD; return Nov 24–30: American $356.50, nonstop / United $408.25, out: 1 stop via IAD, back: 1 stop via IAD; return Dec 1–5: American $310, nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $165, nonstop
Hotels in Boston for these nights (Nov 21–22, 2026 · 1 night · 2 adults, 1 room): 3★ Fairfield Inn & Suites Boston Cambridge, $154 total · 4★ YOTEL Boston, $202 total · 5★ Omni Boston Hotel at the Seaport, $259 total
Sun, Nov 22, 2026 · round trip · return Nov 23: American $310, nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD; return Nov 24–30: American $356.50, nonstop / United $408.25, out: 1 stop via IAD, back: 1 stop via IAD; return Dec 1–6: American $310, nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $165, nonstop
Hotels in Boston for these nights (Nov 22–23, 2026 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $123 total · 4★ Hilton Boston Park Plaza Hotel, $149 total · 5★ Omni Boston Hotel at the Seaport, $202 total
Mon, Nov 23, 2026 · round trip · return Nov 24–30: American $356.50, nonstop / United $408.25, out: 1 stop via IAD, back: 1 stop via IAD; return Dec 1–7: American $310, nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $165, nonstop
Hotels in Boston for these nights (Nov 23 – Dec 1, 2026 · 8 nights · 2 adults, 1 room): 3★ Aloft by Marriott Boston Seaport District, $1,056 total · 4★ Hilton Boston Park Plaza Hotel, $1,248 total · 5★ Omni Boston Hotel at the Seaport, $1,711 total
Tue, Nov 24, 2026 · round trip · return Nov 25–30: American $403, nonstop / United $461.50, out: 1 stop via IAD, back: 1 stop via IAD; return Dec 1–8: American $356.50, nonstop / United $408.25, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $214.50, nonstop
Hotels in Boston for these nights (Nov 24 – Dec 1, 2026 · 7 nights · 2 adults, 1 room): 3★ Aloft by Marriott Boston Seaport District, $925 total · 4★ Hilton Boston Park Plaza Hotel, $1,089 total · 5★ Omni Boston Hotel at the Seaport, $1,509 total
Wed, Nov 25, 2026 · round trip · return Nov 26–30: American $422.50, out: 1 stop via PHL, back: nonstop / United $461.50, out: 1 stop via IAD, back: 1 stop via IAD; return Dec 1–9: American $376, out: 1 stop via PHL, back: nonstop / United $408.25, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $234, out: 1 stop via PHL
Hotels in Boston for these nights (Nov 25 – Dec 1, 2026 · 6 nights · 2 adults, 1 room): 3★ Aloft by Marriott Boston Seaport District, $794 total · 4★ Hilton Boston Park Plaza Hotel, $937 total · 5★ Omni Boston Hotel at the Seaport, $1,309 total
Thu, Nov 26, 2026 · round trip · return Nov 27–30: American $403, nonstop / United $461.50, out: 1 stop via IAD, back: 1 stop via IAD; return Dec 1–10: American $356.50, nonstop / United $408.25, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $214.50, nonstop
Hotels in Boston for these nights (Nov 26 – Dec 1, 2026 · 5 nights · 2 adults, 1 room): 3★ Aloft by Marriott Boston Seaport District, $663 total · 4★ Hilton Boston Park Plaza Hotel, $785 total · 5★ Omni Boston Hotel at the Seaport, $1,104 total
Fri, Nov 27, 2026 · round trip · return Nov 28–30: American $403, nonstop / United $461.50, out: 1 stop via IAD, back: 1 stop via IAD; return Dec 1–11: American $356.50, nonstop / United $408.25, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $214.50, nonstop
Hotels in Boston for these nights (Nov 27 – Dec 1, 2026 · 4 nights · 2 adults, 1 room): 3★ Aloft by Marriott Boston Seaport District, $532 total · 4★ Hilton Boston Park Plaza Hotel, $633 total · 5★ Omni Boston Hotel at the Seaport, $902 total
Sat, Nov 28, 2026 · round trip · return Nov 29–30: American $403, nonstop / United $461.50, out: 1 stop via IAD, back: 1 stop via IAD; return Dec 1–12: American $356.50, nonstop / United $408.25, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $214.50, nonstop
Hotels in Boston for these nights (Nov 28 – Dec 1, 2026 · 3 nights · 2 adults, 1 room): 3★ Aloft by Marriott Boston Seaport District, $401 total · 4★ Hilton Boston Park Plaza Hotel, $480 total · 5★ Omni Boston Hotel at the Seaport, $697 total
Sun, Nov 29, 2026 · round trip · return Nov 30: American $403, nonstop / United $461.50, out: 1 stop via IAD, back: 1 stop via IAD; return Dec 1–13: American $356.50, nonstop / United $408.25, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $214.50, nonstop
Hotels in Boston for these nights (Nov 29 – Dec 1, 2026 · 2 nights · 2 adults, 1 room): 3★ Aloft by Marriott Boston Seaport District, $270 total · 4★ Hilton Boston Park Plaza Hotel, $327 total · 5★ Omni Boston Hotel at the Seaport, $491 total
Mon, Nov 30, 2026 · round trip · return Dec 1–14: American $356.50, nonstop / United $408.25, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $214.50, nonstop
Hotels in Boston for these nights (Nov 30 – Dec 1, 2026 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $137 total · 4★ Hilton Boston Park Plaza Hotel, $173 total · 5★ Omni Boston Hotel at the Seaport, $289 total
Middletown to Boston flights in December 2026: price by departure date
MDT → BOS · USD · 1 adult · economy · published Oct 29, 2026
Tue, Dec 1, 2026 · round trip · return Dec 2–15: American $310, nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $165, nonstop
Hotels in Boston for these nights (Dec 1–2, 2026 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $174 total · 4★ YOTEL Boston, $193 total · 5★ Omni Boston Hotel at the Seaport, $340 total
Wed, Dec 2, 2026 · round trip · return Dec 3–16: American $325, out: 1 stop via PHL, back: nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $180, out: 1 stop via PHL
Hotels in Boston for these nights (Dec 2–3, 2026 · 1 night · 2 adults, 1 room): 3★ Staypineapple, A Delightful Hotel, South End, $177 total · 4★ YOTEL Boston, $212 total · 5★ The Ritz-Carlton, Boston, $398 total
Thu, Dec 3, 2026 · round trip · return Dec 4–17: American $310, nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $165, nonstop
Hotels in Boston for these nights (Dec 3–4, 2026 · 1 night · 2 adults, 1 room): 3★ Staypineapple, A Delightful Hotel, South End, $143 total · 4★ Hilton Boston Park Plaza Hotel, $174 total · 5★ InterContinental Boston by IHG, $361 total
Fri, Dec 4, 2026 · round trip · return Dec 5–18: American $310, nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $165, nonstop
Hotels in Boston for these nights (Dec 4–5, 2026 · 1 night · 2 adults, 1 room): 3★ Staypineapple, A Delightful Hotel, South End, $130 total · 4★ Hilton Boston Park Plaza Hotel, $168 total · 5★ InterContinental Boston by IHG, $325 total
Sat, Dec 5, 2026 · round trip · return Dec 6–18: American $310, nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD; return Dec 19: American $348.75, nonstop / United $399.38, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $165, nonstop
Hotels in Boston for these nights (Dec 5–6, 2026 · 1 night · 2 adults, 1 room): 3★ Staypineapple, A Delightful Hotel, South End, $179 total · 4★ Hilton Boston Park Plaza Hotel, $166 total · 5★ Omni Boston Hotel at the Seaport, $266 total
Sun, Dec 6, 2026 · round trip · return Dec 7–18: American $310, nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD; return Dec 19–20: American $348.75, nonstop / United $399.38, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $165, nonstop
Hotels in Boston for these nights (Dec 6–7, 2026 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $119 total · 4★ Hilton Boston Park Plaza Hotel, $161 total · 5★ Omni Boston Hotel at the Seaport, $266 total
Mon, Dec 7, 2026 · round trip · return Dec 8–18: American $310, nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD; return Dec 19–21: American $348.75, nonstop / United $399.38, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $165, nonstop
Hotels in Boston for these nights (Dec 7–8, 2026 · 1 night · 2 adults, 1 room): 3★ Staypineapple, A Delightful Hotel, South End, $122 total · 4★ Hilton Boston Park Plaza Hotel, $170 total · 5★ Omni Boston Hotel at the Seaport, $290 total
Tue, Dec 8, 2026 · round trip · return Dec 9–18: American $310, nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD; return Dec 19–22: American $348.75, nonstop / United $399.38, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $165, nonstop
Hotels in Boston for these nights (Dec 8–9, 2026 · 1 night · 2 adults, 1 room): 3★ Staypineapple, A Delightful Hotel, South End, $126 total · 4★ Hilton Boston Park Plaza Hotel, $181 total · 5★ Omni Boston Hotel at the Seaport, $287 total
Wed, Dec 9, 2026 · round trip · return Dec 10–18: American $325, out: 1 stop via PHL, back: nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD; return Dec 19–23: American $363.75, out: 1 stop via PHL, back: nonstop / United $399.38, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $180, out: 1 stop via PHL
Hotels in Boston for these nights (Dec 9–10, 2026 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $161 total · 4★ Hilton Boston Park Plaza Hotel, $184 total · 5★ Omni Boston Hotel at the Seaport, $309 total
Thu, Dec 10, 2026 · round trip · return Dec 11–18: American $310, nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD; return Dec 19–24: American $348.75, nonstop / United $399.38, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $165, nonstop
Hotels in Boston for these nights (Dec 10–11, 2026 · 1 night · 2 adults, 1 room): 3★ Staypineapple, A Delightful Hotel, South End, $155 total · 4★ YOTEL Boston, $165 total · 5★ Omni Boston Hotel at the Seaport, $289 total
Fri, Dec 11, 2026 · round trip · return Dec 12–18: American $310, nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD; return Dec 19–25: American $348.75, nonstop / United $399.38, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $165, nonstop
Hotels in Boston for these nights (Dec 11–12, 2026 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $145 total · 4★ Hilton Boston Park Plaza Hotel, $159 total · 5★ Omni Boston Hotel at the Seaport, $310 total
Sat, Dec 12, 2026 · round trip · return Dec 13–18: American $310, nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD; return Dec 19–26: American $348.75, nonstop / United $399.38, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $165, nonstop
Hotels in Boston for these nights (Dec 12–13, 2026 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $148 total · 4★ Hilton Boston Park Plaza Hotel, $161 total · 5★ Omni Boston Hotel at the Seaport, $302 total
Sun, Dec 13, 2026 · round trip · return Dec 14–18: American $310, nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD; return Dec 19–27: American $348.75, nonstop / United $399.38, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $165, nonstop
Hotels in Boston for these nights (Dec 13–14, 2026 · 1 night · 2 adults, 1 room): 3★ Staypineapple, A Delightful Hotel, South End, $115 total · 4★ Hilton Boston Park Plaza Hotel, $150 total · 5★ Omni Boston Hotel at the Seaport, $239 total
Mon, Dec 14, 2026 · round trip · return Dec 15–18: American $310, nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD; return Dec 19–28: American $348.75, nonstop / United $399.38, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $165, nonstop
Hotels in Boston for these nights (Dec 14–15, 2026 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $118 total · 4★ Hilton Boston Park Plaza Hotel, $150 total · 5★ Omni Boston Hotel at the Seaport, $244 total
Tue, Dec 15, 2026 · round trip · return Dec 16–18: American $310, nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD; return Dec 19–29: American $348.75, nonstop / United $399.38, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $165, nonstop
Hotels in Boston for these nights (Dec 15–16, 2026 · 1 night · 2 adults, 1 room): 3★ Staypineapple, A Delightful Hotel, South End, $126 total · 4★ Hilton Boston Park Plaza Hotel, $152 total · 5★ InterContinental Boston by IHG, $324 total
Wed, Dec 16, 2026 · round trip · return Dec 17–18: American $325, out: 1 stop via PHL, back: nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD; return Dec 19–30: American $363.75, out: 1 stop via PHL, back: nonstop / United $399.38, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $180, out: 1 stop via PHL
Hotels in Boston for these nights (Dec 16–17, 2026 · 1 night · 2 adults, 1 room): 3★ Staypineapple, A Delightful Hotel, South End, $126 total · 4★ Hilton Boston Park Plaza Hotel, $152 total · 5★ InterContinental Boston by IHG, $318 total
Thu, Dec 17, 2026 · round trip · return Dec 18: American $310, nonstop / United $355, out: 1 stop via IAD, back: 1 stop via IAD; return Dec 19–31: American $348.75, nonstop / United $399.38, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $165, nonstop
Hotels in Boston for these nights (Dec 17–18, 2026 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $116 total · 4★ Hilton Boston Park Plaza Hotel, $154 total · 5★ InterContinental Boston by IHG, $279 total
Fri, Dec 18, 2026 · round trip · return Dec 19–31: American $348.75, nonstop / United $399.38, out: 1 stop via IAD, back: 1 stop via IAD; return Jan 1, 2027: American $337.90, nonstop / United $386.95, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $165, nonstop
Hotels in Boston for these nights (Dec 18 – Jan 1, 2027 · 14 nights · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $1,836 total · 4★ Hilton Boston Park Plaza Hotel, $2,310 total · 5★ Omni Boston Hotel at the Seaport, $3,078 total
Sat, Dec 19, 2026 · round trip · return Dec 20–31: American $387.50, nonstop / United $443.76, out: 1 stop via IAD, back: 1 stop via IAD; return Jan 1–2, 2027: American $376.65, nonstop / United $431.33, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $206.25, nonstop
Hotels in Boston for these nights (Dec 19 – Jan 1, 2027 · 13 nights · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $1,703 total · 4★ Hilton Boston Park Plaza Hotel, $2,152 total · 5★ Omni Boston Hotel at the Seaport, $2,837 total
Sun, Dec 20, 2026 · round trip · return Dec 21–31: American $387.50, nonstop / United $443.76, out: 1 stop via IAD, back: 1 stop via IAD; return Jan 1–3, 2027: American $376.65, nonstop / United $431.33, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $206.25, nonstop
Hotels in Boston for these nights (Dec 20 – Jan 1, 2027 · 12 nights · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $1,571 total · 4★ Hilton Boston Park Plaza Hotel, $1,994 total · 5★ Omni Boston Hotel at the Seaport, $2,594 total
Mon, Dec 21, 2026 · round trip · return Dec 22–31: American $387.50, nonstop / United $443.76, out: 1 stop via IAD, back: 1 stop via IAD; return Jan 1–3, 2027: American $376.65, nonstop / United $431.33, out: 1 stop via IAD, back: 1 stop via IAD; return Jan 4, 2027: American $341, nonstop / United $390.51, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $206.25, nonstop
Hotels in Boston for these nights (Dec 21 – Jan 4, 2027 · 14 nights · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $1,846 total · 4★ Hilton Boston Park Plaza Hotel, $2,330 total · 5★ Omni Boston Hotel at the Seaport, $3,148 total
Tue, Dec 22, 2026 · round trip · return Dec 23–31: American $387.50, nonstop / United $443.76, out: 1 stop via IAD, back: 1 stop via IAD; return Jan 1–3, 2027: American $376.65, nonstop / United $431.33, out: 1 stop via IAD, back: 1 stop via IAD; return Jan 4–5, 2027: American $341, nonstop / United $390.51, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $206.25, nonstop
Hotels in Boston for these nights (Dec 22 – Jan 4, 2027 · 13 nights · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $1,728 total · 4★ Hilton Boston Park Plaza Hotel, $2,166 total · 5★ Omni Boston Hotel at the Seaport, $2,946 total
Wed, Dec 23, 2026 · round trip · return Dec 24–31: American $406.25, out: 1 stop via PHL, back: nonstop / United $443.76, out: 1 stop via IAD, back: 1 stop via IAD; return Jan 1–3, 2027: American $395.40, out: 1 stop via PHL, back: nonstop / United $431.33, out: 1 stop via IAD, back: 1 stop via IAD; return Jan 4–6, 2027: American $359.75, out: 1 stop via PHL, back: nonstop / United $390.51, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $225, out: 1 stop via PHL
Hotels in Boston for these nights (Dec 23 – Jan 4, 2027 · 12 nights · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $1,609 total · 4★ Hilton Boston Park Plaza Hotel, $2,006 total · 5★ Omni Boston Hotel at the Seaport, $2,742 total
Thu, Dec 24, 2026 · round trip · return Dec 25–31: American $387.50, nonstop / United $443.76, out: 1 stop via IAD, back: 1 stop via IAD; return Jan 1–3, 2027: American $376.65, nonstop / United $431.33, out: 1 stop via IAD, back: 1 stop via IAD; return Jan 4–7, 2027: American $341, nonstop / United $390.51, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $206.25, nonstop
Hotels in Boston for these nights (Dec 24 – Jan 4, 2027 · 11 nights · 2 adults, 1 room): 3★ Aloft by Marriott Boston Seaport District, $1,491 total · 4★ Hilton Boston Park Plaza Hotel, $1,846 total · 5★ Omni Boston Hotel at the Seaport, $2,541 total
Fri, Dec 25, 2026 · round trip · return Dec 26–31: American $387.50, nonstop / United $443.76, out: 1 stop via IAD, back: 1 stop via IAD; return Jan 1–3, 2027: American $376.65, nonstop / United $431.33, out: 1 stop via IAD, back: 1 stop via IAD; return Jan 4–8, 2027: American $341, nonstop / United $390.51, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $206.25, nonstop
Hotels in Boston for these nights (Dec 25 – Jan 4, 2027 · 10 nights · 2 adults, 1 room): 3★ Aloft by Marriott Boston Seaport District, $1,364 total · 4★ Hilton Boston Park Plaza Hotel, $1,682 total · 5★ Omni Boston Hotel at the Seaport, $2,341 total
Sat, Dec 26, 2026 · round trip · return Dec 27–31: American $387.50, nonstop / United $443.76, out: 1 stop via IAD, back: 1 stop via IAD; return Jan 1–3, 2027: American $376.65, nonstop / United $431.33, out: 1 stop via IAD, back: 1 stop via IAD; return Jan 4–9, 2027: American $341, nonstop / United $390.51, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $206.25, nonstop
Hotels in Boston for these nights (Dec 26 – Jan 4, 2027 · 9 nights · 2 adults, 1 room): 3★ Aloft by Marriott Boston Seaport District, $1,237 total · 4★ Hilton Boston Park Plaza Hotel, $1,523 total · 5★ Omni Boston Hotel at the Seaport, $2,140 total
Sun, Dec 27, 2026 · round trip · return Dec 28–31: American $387.50, nonstop / United $443.76, out: 1 stop via IAD, back: 1 stop via IAD; return Jan 1–3, 2027: American $376.65, nonstop / United $431.33, out: 1 stop via IAD, back: 1 stop via IAD; return Jan 4–10, 2027: American $341, nonstop / United $390.51, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $206.25, nonstop
Hotels in Boston for these nights (Dec 27 – Jan 4, 2027 · 8 nights · 2 adults, 1 room): 3★ Aloft by Marriott Boston Seaport District, $1,106 total · 4★ Hilton Boston Park Plaza Hotel, $1,365 total · 5★ Omni Boston Hotel at the Seaport, $1,938 total
Mon, Dec 28, 2026 · round trip · return Dec 29–31: American $387.50, nonstop / United $443.76, out: 1 stop via IAD, back: 1 stop via IAD; return Jan 1–3, 2027: American $376.65, nonstop / United $431.33, out: 1 stop via IAD, back: 1 stop via IAD; return Jan 4–11, 2027: American $341, nonstop / United $390.51, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $206.25, nonstop
Hotels in Boston for these nights (Dec 28 – Jan 4, 2027 · 7 nights · 2 adults, 1 room): 3★ Aloft by Marriott Boston Seaport District, $979 total · 4★ Hilton Boston Park Plaza Hotel, $1,203 total · 5★ Omni Boston Hotel at the Seaport, $1,719 total
Tue, Dec 29, 2026 · round trip · return Dec 30–31: American $387.50, nonstop / United $443.76, out: 1 stop via IAD, back: 1 stop via IAD; return Jan 1–3, 2027: American $376.65, nonstop / United $431.33, out: 1 stop via IAD, back: 1 stop via IAD; return Jan 4–12, 2027: American $341, nonstop / United $390.51, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $206.25, nonstop
Hotels in Boston for these nights (Dec 29 – Jan 4, 2027 · 6 nights · 2 adults, 1 room): 3★ Aloft by Marriott Boston Seaport District, $852 total · 4★ Hilton Boston Park Plaza Hotel, $1,041 total · 5★ Omni Boston Hotel at the Seaport, $1,500 total
Wed, Dec 30, 2026 · round trip · return Dec 31: American $406.25, out: 1 stop via PHL, back: nonstop / United $443.76, out: 1 stop via IAD, back: 1 stop via IAD; return Jan 1–3, 2027: American $395.40, out: 1 stop via PHL, back: nonstop / United $431.33, out: 1 stop via IAD, back: 1 stop via IAD; return Jan 4–13, 2027: American $359.75, out: 1 stop via PHL, back: nonstop / United $390.51, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $225, out: 1 stop via PHL
Hotels in Boston for these nights (Dec 30 – Jan 4, 2027 · 5 nights · 2 adults, 1 room): 3★ Aloft by Marriott Boston Seaport District, $725 total · 4★ Hilton Boston Park Plaza Hotel, $882 total · 5★ Omni Boston Hotel at the Seaport, $1,281 total
Thu, Dec 31, 2026 · round trip · return Jan 1–3, 2027: American $376.65, nonstop / United $431.33, out: 1 stop via IAD, back: 1 stop via IAD; return Jan 4–14, 2027: American $341, nonstop / United $390.51, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $206.25, nonstop
Hotels in Boston for these nights (Dec 31 – Jan 4, 2027 · 4 nights · 2 adults, 1 room): 3★ Aloft by Marriott Boston Seaport District, $598 total · 4★ Hilton Boston Park Plaza Hotel, $720 total · 5★ Omni Boston Hotel at the Seaport, $1,063 total
Middletown to Boston flights in January 2027: price by departure date
MDT → BOS · USD · 1 adult · economy · published Oct 29, 2026
Fri, Jan 1, 2027 · round trip · return Jan 2–3: American $365.80, nonstop / United $418.90, out: 1 stop via IAD, back: 1 stop via IAD; return Jan 4–15: American $330.15, nonstop / United $378.08, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $194.70, nonstop
Hotels in Boston for these nights (Jan 1–4, 2027 · 3 nights · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $394 total · 4★ Hyatt Regency Boston, $495 total · 5★ Omni Boston Hotel at the Seaport, $758 total
Sat, Jan 2, 2027 · round trip · return Jan 3: American $365.80, nonstop / United $418.90, out: 1 stop via IAD, back: 1 stop via IAD; return Jan 4–16: American $330.15, nonstop / United $378.08, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $194.70, nonstop
Hotels in Boston for these nights (Jan 2–4, 2027 · 2 nights · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $261 total · 4★ Hilton Boston Park Plaza Hotel, $327 total · 5★ Omni Boston Hotel at the Seaport, $480 total
Sun, Jan 3, 2027 · round trip · return Jan 4–17: American $330.15, nonstop / United $378.08, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $194.70, nonstop
Hotels in Boston for these nights (Jan 3–4, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $119 total · 4★ The Dagny Boston, $165 total · 5★ InterContinental Boston by IHG, $249 total
Mon, Jan 4, 2027 · round trip · return Jan 5–18: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Jan 4–5, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $119 total · 4★ YOTEL Boston, $163 total · 5★ InterContinental Boston by IHG, $251 total
Tue, Jan 5, 2027 · round trip · return Jan 6–19: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Jan 5–6, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $119 total · 4★ Hilton Boston Park Plaza Hotel, $162 total · 5★ InterContinental Boston by IHG, $271 total
Wed, Jan 6, 2027 · round trip · return Jan 7–20: American $308.75, out: 1 stop via PHL, back: nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $171, out: 1 stop via PHL
Hotels in Boston for these nights (Jan 6–7, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $119 total · 4★ Hilton Boston Park Plaza Hotel, $162 total · 5★ Omni Boston Hotel at the Seaport, $275 total
Thu, Jan 7, 2027 · round trip · return Jan 8–21: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Jan 7–8, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $119 total · 4★ Hilton Boston Park Plaza Hotel, $162 total · 5★ Omni Boston Hotel at the Seaport, $271 total
Fri, Jan 8, 2027 · round trip · return Jan 9–22: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Jan 8–9, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $129 total · 4★ Hilton Boston Park Plaza Hotel, $141 total · 5★ InterContinental Boston by IHG, $268 total
Sat, Jan 9, 2027 · round trip · return Jan 10–23: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Jan 9–10, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $126 total · 4★ Hilton Boston Park Plaza Hotel, $141 total · 5★ InterContinental Boston by IHG, $272 total
Sun, Jan 10, 2027 · round trip · return Jan 11–24: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Jan 10–11, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $119 total · 4★ Hilton Boston Park Plaza Hotel, $140 total · 5★ InterContinental Boston by IHG, $281 total
Mon, Jan 11, 2027 · round trip · return Jan 12–25: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Jan 11–12, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $119 total · 4★ Hilton Boston Park Plaza Hotel, $163 total · 5★ The Liberty, a Marriott Luxury Collection Hotel, Boston, $305 total
Tue, Jan 12, 2027 · round trip · return Jan 13–26: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Jan 12–13, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $119 total · 4★ Hilton Boston Park Plaza Hotel, $167 total · 5★ Omni Boston Hotel at the Seaport, $327 total
Wed, Jan 13, 2027 · round trip · return Jan 14–27: American $308.75, out: 1 stop via PHL, back: nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $171, out: 1 stop via PHL
Hotels in Boston for these nights (Jan 13–14, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $133 total · 4★ Hilton Boston Park Plaza Hotel, $162 total · 5★ Omni Boston Hotel at the Seaport, $291 total
Thu, Jan 14, 2027 · round trip · return Jan 15–28: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Jan 14–15, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $119 total · 4★ Hyatt Regency Boston, $115 total · 5★ The Liberty, a Marriott Luxury Collection Hotel, Boston, $315 total
Fri, Jan 15, 2027 · round trip · return Jan 16–29: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Jan 15–16, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $126 total · 4★ Hilton Boston Park Plaza Hotel, $163 total · 5★ InterContinental Boston by IHG, $350 total
Sat, Jan 16, 2027 · round trip · return Jan 17–30: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Jan 16–17, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $133 total · 4★ Hilton Boston Park Plaza Hotel, $162 total · 5★ The Langham, Boston, $349 total
Sun, Jan 17, 2027 · round trip · return Jan 18–31: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Jan 17–18, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $119 total · 4★ Hilton Boston Park Plaza Hotel, $160 total · 5★ The Liberty, a Marriott Luxury Collection Hotel, Boston, $283 total
Mon, Jan 18, 2027 · round trip · return Jan 19–Feb 1: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Jan 18–19, 2027 · 1 night · 2 adults, 1 room): 3★ Staypineapple, A Delightful Hotel, South End, $123 total · 4★ Hilton Boston Park Plaza Hotel, $162 total · 5★ InterContinental Boston by IHG, $258 total
Tue, Jan 19, 2027 · round trip · return Jan 20–Feb 2: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Jan 19–20, 2027 · 1 night · 2 adults, 1 room): 3★ Staypineapple, A Delightful Hotel, South End, $120 total · 4★ Hilton Boston Park Plaza Hotel, $165 total · 5★ The Liberty, a Marriott Luxury Collection Hotel, Boston, $340 total
Wed, Jan 20, 2027 · round trip · return Jan 21–Feb 3: American $308.75, out: 1 stop via PHL, back: nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $171, out: 1 stop via PHL
Hotels in Boston for these nights (Jan 20–21, 2027 · 1 night · 2 adults, 1 room): 3★ Staypineapple, A Delightful Hotel, South End, $121 total · 4★ Hilton Boston Park Plaza Hotel, $164 total · 5★ The Liberty, a Marriott Luxury Collection Hotel, Boston, $325 total
Thu, Jan 21, 2027 · round trip · return Jan 22–Feb 4: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Jan 21–22, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $142 total · 4★ Hilton Boston Park Plaza Hotel, $160 total · 5★ The Liberty, a Marriott Luxury Collection Hotel, Boston, $320 total
Fri, Jan 22, 2027 · round trip · return Jan 23–Feb 5: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Jan 22–23, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $126 total · 4★ Hilton Boston Park Plaza Hotel, $143 total · 5★ InterContinental Boston by IHG, $280 total
Sat, Jan 23, 2027 · round trip · return Jan 24–Feb 6: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Jan 23–24, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $125 total · 4★ Hilton Boston Park Plaza Hotel, $141 total · 5★ InterContinental Boston by IHG, $268 total
Sun, Jan 24, 2027 · round trip · return Jan 25–Feb 7: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Jan 24–25, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $119 total · 4★ Hilton Boston Park Plaza Hotel, $155 total · 5★ InterContinental Boston by IHG, $256 total
Mon, Jan 25, 2027 · round trip · return Jan 26–Feb 8: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Jan 25–26, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $119 total · 4★ Hilton Boston Park Plaza Hotel, $155 total · 5★ Omni Boston Hotel at the Seaport, $291 total
Tue, Jan 26, 2027 · round trip · return Jan 27–Feb 9: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Jan 26–27, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $119 total · 4★ Hilton Boston Park Plaza Hotel, $153 total · 5★ Omni Boston Hotel at the Seaport, $336 total
Wed, Jan 27, 2027 · round trip · return Jan 28–Feb 10: American $308.75, out: 1 stop via PHL, back: nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $171, out: 1 stop via PHL
Hotels in Boston for these nights (Jan 27–28, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $119 total · 4★ Hilton Boston Park Plaza Hotel, $154 total · 5★ The Liberty, a Marriott Luxury Collection Hotel, Boston, $330 total
Thu, Jan 28, 2027 · round trip · return Jan 29–Feb 11: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Jan 28–29, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $119 total · 4★ Hilton Boston Park Plaza Hotel, $154 total · 5★ The Liberty, a Marriott Luxury Collection Hotel, Boston, $326 total
Fri, Jan 29, 2027 · round trip · return Jan 30–Feb 11: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD; return Feb 12: American $308.45, nonstop / United $353.23, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Jan 29–30, 2027 · 1 night · 2 adults, 1 room): 3★ Staypineapple, A Delightful Hotel, South End, $120 total · 4★ Hilton Boston Park Plaza Hotel, $151 total · 5★ InterContinental Boston by IHG, $279 total
Sat, Jan 30, 2027 · round trip · return Jan 31–Feb 11: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD; return Feb 12–13: American $308.45, nonstop / United $353.23, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Jan 30–31, 2027 · 1 night · 2 adults, 1 room): 3★ Staypineapple, A Delightful Hotel, South End, $121 total · 4★ Hilton Boston Park Plaza Hotel, $150 total · 5★ InterContinental Boston by IHG, $277 total
Sun, Jan 31, 2027 · round trip · return Feb 1–11: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD; return Feb 12–14: American $308.45, nonstop / United $353.23, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Jan 31 – Feb 1, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $119 total · 4★ Hilton Boston Park Plaza Hotel, $139 total · 5★ InterContinental Boston by IHG, $262 total
Middletown to Boston flights in February 2027: price by departure date
MDT → BOS · USD · 1 adult · economy · published Oct 29, 2026
Mon, Feb 1, 2027 · round trip · return Feb 2–11: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD; return Feb 12–15: American $308.45, nonstop / United $353.23, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Feb 1–2, 2027 · 1 night · 2 adults, 1 room): 3★ Staypineapple, A Delightful Hotel, South End, $120 total · 4★ Hilton Boston Park Plaza Hotel, $167 total · 5★ InterContinental Boston by IHG, $314 total
Tue, Feb 2, 2027 · round trip · return Feb 3–11: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD; return Feb 12–16: American $308.45, nonstop / United $353.23, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Feb 2–3, 2027 · 1 night · 2 adults, 1 room): 3★ Staypineapple, A Delightful Hotel, South End, $121 total · 4★ Hilton Boston Park Plaza Hotel, $164 total · 5★ Omni Boston Hotel at the Seaport, $274 total
Wed, Feb 3, 2027 · round trip · return Feb 4–11: American $308.75, out: 1 stop via PHL, back: nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD; return Feb 12–16: American $322.70, out: 1 stop via PHL, back: nonstop / United $353.23, out: 1 stop via IAD, back: 1 stop via IAD; return Feb 17: American $308.75, out: 1 stop via PHL, back: nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $171, out: 1 stop via PHL
Hotels in Boston for these nights (Feb 3–4, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $119 total · 4★ Hilton Boston Park Plaza Hotel, $163 total · 5★ Omni Boston Hotel at the Seaport, $367 total
Thu, Feb 4, 2027 · round trip · return Feb 5–11: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD; return Feb 12–16: American $308.45, nonstop / United $353.23, out: 1 stop via IAD, back: 1 stop via IAD; return Feb 17–18: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Feb 4–5, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $119 total · 4★ Hilton Boston Park Plaza Hotel, $160 total · 5★ Omni Boston Hotel at the Seaport, $352 total
Fri, Feb 5, 2027 · round trip · return Feb 6–11: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD; return Feb 12–16: American $308.45, nonstop / United $353.23, out: 1 stop via IAD, back: 1 stop via IAD; return Feb 17–19: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Feb 5–6, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $126 total · 4★ Hilton Boston Park Plaza Hotel, $142 total · 5★ InterContinental Boston by IHG, $320 total
Sat, Feb 6, 2027 · round trip · return Feb 7–11: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD; return Feb 12–16: American $308.45, nonstop / United $353.23, out: 1 stop via IAD, back: 1 stop via IAD; return Feb 17–20: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Feb 6–7, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $121 total · 4★ Hilton Boston Park Plaza Hotel, $143 total · 5★ InterContinental Boston by IHG, $323 total
Sun, Feb 7, 2027 · round trip · return Feb 8–11: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD; return Feb 12–16: American $308.45, nonstop / United $353.23, out: 1 stop via IAD, back: 1 stop via IAD; return Feb 17–21: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Feb 7–8, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $119 total · 4★ Hilton Boston Park Plaza Hotel, $139 total · 5★ The Liberty, a Marriott Luxury Collection Hotel, Boston, $289 total
Mon, Feb 8, 2027 · round trip · return Feb 9–11: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD; return Feb 12–16: American $308.45, nonstop / United $353.23, out: 1 stop via IAD, back: 1 stop via IAD; return Feb 17–22: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Feb 8–9, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $119 total · 4★ Hilton Boston Park Plaza Hotel, $162 total · 5★ The Liberty, a Marriott Luxury Collection Hotel, Boston, $326 total
Tue, Feb 9, 2027 · round trip · return Feb 10–11: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD; return Feb 12–16: American $308.45, nonstop / United $353.23, out: 1 stop via IAD, back: 1 stop via IAD; return Feb 17–23: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Feb 9–10, 2027 · 1 night · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $122 total · 4★ Hilton Boston Park Plaza Hotel, $165 total · 5★ Omni Boston Hotel at the Seaport, $344 total
Wed, Feb 10, 2027 · round trip · return Feb 11: American $308.75, out: 1 stop via PHL, back: nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD; return Feb 12–16: American $322.70, out: 1 stop via PHL, back: nonstop / United $353.23, out: 1 stop via IAD, back: 1 stop via IAD; return Feb 17–24: American $308.75, out: 1 stop via PHL, back: nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $171, out: 1 stop via PHL
Hotels in Boston for these nights (Feb 10–11, 2027 · 1 night · 2 adults, 1 room): 3★ Staypineapple, A Delightful Hotel, South End, $120 total · 4★ Hilton Boston Park Plaza Hotel, $160 total · 5★ Omni Boston Hotel at the Seaport, $344 total
Thu, Feb 11, 2027 · round trip · return Feb 12–16: American $308.45, nonstop / United $353.23, out: 1 stop via IAD, back: 1 stop via IAD; return Feb 17–25: American $294.50, nonstop / United $337.26, out: 1 stop via IAD, back: 1 stop via IAD · one-way: American $156.75, nonstop
Hotels in Boston for these nights (Feb 11–17, 2027 · 6 nights · 2 adults, 1 room): 3★ Staypineapple, A Delightful Hotel, South End, $963 total · 4★ Hilton Boston Park Plaza Hotel, $924 total · 5★ Omni Boston Hotel at the Seaport, $1,912 total
Middletown to Boston nonstop flights, airlines and connections
Yes, American flies it nonstop. In the 21 departure dates we searched from Nov 10 to Sep 11, a nonstop from Middletown flew on 16: Saturdays 7 of 12, Fridays 4 of 4, Tuesdays 2 of 2, Thursdays 2 of 2 and Sundays 1 of 1. The nonstops were American (AA4708, AA4684, AA4714). These are the airlines seen in the saved flights.
- American: Nonstop to Boston
| Departure date | Itineraries searched | Nonstop | Airlines and flights |
|---|---|---|---|
| Tue Nov 10 | 24 | yes, both ways | American AA4708 |
| Sat Nov 21 | 24 | yes, both ways | American AA4708 |
| Thu Dec 3 | 24 | yes, both ways | American AA4708 |
| Tue Dec 8 | 24 | yes, both ways | American AA4708 |
| Sat Jan 9 | 24 | none seen | — |
| Sat Jan 16 | 24 | none seen | — |
| Fri Feb 12 | 24 | yes, both ways | American AA4684 |
| Sat Feb 13 | 24 | none seen | — |
| Sat Mar 6 | 24 | none seen | — |
| Sat Mar 13 | 24 | none seen | — |
| Thu Mar 25 | 24 | yes, both ways | American AA4684 |
| Sat Apr 10 | 24 | yes, both ways | American AA4714 |
| Sun Apr 18 | 24 | yes | American AA4714 |
| Sat May 8 | 24 | yes, both ways | American AA4714 |
| Fri May 28 | 24 | yes, both ways | American AA4714 |
| Sat Jun 12 | 24 | yes, both ways | American AA4714 |
| Fri Jul 2 | 24 | yes, both ways | American AA4714 |
| Sat Jul 10 | 24 | yes, both ways | American AA4714 |
| Sat Aug 7 | 24 | yes, both ways | American AA4714 |
| Fri Sep 3 | 24 | yes, both ways | American AA4714 |
| Sat Sep 11 | 24 | yes, both ways | American AA4714 |
Every departure date searched for this route in the last 14 days, from every itinerary those searches returned. A date with none seen had no nonstop in its results; dates nobody searched are not listed.
Why book Middletown to Boston flights with Axel
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How we checked Middletown to Boston prices
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Airports covered: MDT → BOS. Each example names its actual airports.
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Planning: When to book Thanksgiving flights · Flying in December: prices, crowds and delays · How far in advance to book flights · The cheapest days of the week to fly and to book.
Trip ideas from Middletown with Boston (BOS)
- Best places to fly from Middletown for Thanksgiving: fly Nov 21 – Nov 28, 2026
- Cheapest places to fly from Middletown for 4 days: fly Dec 3 – Dec 6, 2026
- Cheapest places to fly from Middletown in December: fly Dec 5 – Dec 12, 2026
- Best places to fly from Middletown for Christmas: fly Dec 19 – Dec 26, 2026
- Cheapest places to fly from Middletown for two weeks: fly Jan 9 – Jan 23, 2027
- Best places to fly from Middletown for MLK weekend: fly Jan 15 – Jan 18, 2027
- Cheapest places to fly from Middletown in January: fly Jan 16 – Jan 23, 2027
- Best places to fly from Middletown for Presidents' Day weekend: fly Feb 12 – Feb 16, 2027
- Cheapest places to fly from Middletown in February: fly Feb 13 – Feb 20, 2027
- Cheapest places to fly from Middletown in March: fly Mar 6 – Mar 13, 2027
- Best places to fly from Middletown for spring break: fly Mar 13 – Mar 20, 2027
- Best places to fly from Middletown for Easter weekend: fly Mar 25 – Mar 29, 2027
- Cheapest places to fly from Middletown in April: fly Apr 10 – Apr 17, 2027
- Marathon trips from Middletown: New York, Tokyo, Boston, London, Berlin and more: fly Apr 18 – Apr 20, 2027
- Cheapest places to fly from Middletown in May: fly May 8 – May 15, 2027
- Best places to fly from Middletown for Memorial Day weekend: fly May 28 – May 31, 2027
- Cheapest places to fly from Middletown in June: fly Jun 12 – Jun 19, 2027
- Best places to fly from Middletown for July 4th weekend: fly Jul 2 – Jul 5, 2027
- Fourth of July trips from Middletown: fly Jul 2 – Jul 5, 2027
- Cheapest places to fly from Middletown in July: fly Jul 10 – Jul 17, 2027
- Cheapest places to fly from Middletown in August: fly Aug 7 – Aug 14, 2027
- Best places to fly from Middletown for Labor Day weekend: fly Sep 3 – Sep 6, 2027
- Cheapest places to fly from Middletown in September: fly Sep 11 – Sep 18, 2027
- Cheapest places to fly from Middletown for a week
- Cheapest places to fly from Middletown in November
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Source: https://helloaxel.com/en/flights/from-middletown-mdt-to-boston-bos
Hotels in Boston with Axel
Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Boston has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.
Where to stay: Where to stay in Boston: the 7 best neighborhoods, ranked · Boston hotels where a family of four can share one room
Hotel details in Boston: AC Hotel by Marriott Boston Cleveland Circle · Hotel Commonwealth · Maverick Suites at 402 Columbus Ave · All 137 hotels in Boston
Near BOS: Hawthorne Hotel (Salem) · Four Points by Sheraton Boston Newton (Newton)
For AI assistants
- This page: Middletown to Boston (BOS) flight deals. Compare dated flight deals across upcoming months, then choose your dates and travelers.
- Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.