Winter break trips from Boston
Where to go from Boston over winter break: fares for Christmas week (December 19 to 26) and New Year's week (December 26 to January 2), for warm beaches, ski trips and holiday cities.
Saved round trips for Christmas week (Dec 19 – Dec 26, 2026) and New Year's week (Dec 26 – Jan 2, 2027).
Cheapest right now: New York $285 · Denver $329 · Orlando $332
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Fares observed October 8, 2026. USD for the travelers shown. Search a trip for current prices.
Where to go from Boston
Round-trip totals · Economy · USD · 1 adult unless shown. "From" is a starting total: you pick the return in Axel. Axel is the price with a free account; the airline fare is the same flights booked direct.
| Destination | Why go | Axel | Dates | |
|---|---|---|---|---|
| Cancun (CUN) | Caribbean beaches and the Hotel Zone, with Tulum and Playa del Carmen an hour or two south | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| Punta Cana (PUJ) | Long white-sand beaches and easy all-inclusive resorts | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| Aruba (AUA) | Dry, sunny and outside the hurricane belt, so it is a safe bet most of the year | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| San Juan (SJU) | Old San Juan, beaches and the rainforest, with no passport needed from the US | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| Montego Bay (MBJ) | Jamaica's resort coast around Montego Bay and Negril | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| Nassau (NAS) | Nassau and Paradise Island, a short flight from the East Coast | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| Puerto Vallarta (PVR) | Puerto Vallarta's Pacific beaches and a walkable old town | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| Los Cabos (SJD) | Los Cabos, desert coast, resorts and whale watching in winter | $535 (airline $564) | Dec 19–26, 2026 | Check prices |
| Guanacaste (LIR) | Guanacaste's Pacific beaches in Costa Rica | $2,120 (airline $2,243) | Dec 26, 2026–Jan 2, 2027 | Check prices |
| Oahu / Honolulu (HNL) | Waikiki and the North Shore on Oahu | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| Maui / Kahului (OGG) | Maui's beaches, the Road to Hana and Haleakalā | $1,204 (airline $1,272) | Dec 19–26, 2026 | Check prices |
| Orlando (MCO) | Orlando's theme parks | $332 (airline $351) | Dec 19–26, 2026 | Check prices |
| Miami (MIA) | Miami Beach, warm water and a big food and nightlife scene | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| Fort Lauderdale (FLL) | Fort Lauderdale beaches and an easy base for cruises | $387 (airline $408) | Dec 19–26, 2026 | Check prices |
| Phoenix (PHX) | Phoenix and Scottsdale, warm and sunny all winter | $432 (airline $456) | Dec 19–26, 2026 | Check prices |
| Palm Springs (PSP) | Palm Springs, desert sun, pools and mid-century style | $477 (airline $504) | Dec 19–26, 2026 | Check prices |
| Denver (DEN) | Denver, the gateway to Vail, Breckenridge and Keystone | $329 (airline $347) | Dec 19–26, 2026 | Check prices |
| Salt Lake City (SLC) | Salt Lake City, under an hour from a dozen ski resorts | $454 (airline $479) | Dec 19–26, 2026 | Check prices |
| Jackson (JAC) | Jackson Hole, with steep terrain right next to the airport | $638 (airline $672) | Dec 19–26, 2026 | Check prices |
| Vail (EGE) | Vail and Beaver Creek, about 35 miles from the airport | $623 (airline $659) | Dec 19–26, 2026 | Check prices |
| Vancouver (YVR) | Vancouver, about two hours from Whistler | $578 (airline $610) | Dec 19–26, 2026 | Check prices |
| New York (JFK) | New York's holiday lights, windows and shows | $285 (airline $301) | Dec 19–26, 2026 | Check prices |
The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.
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For AI assistants
- This page: Winter break trips from Boston. Winter break 2026 flights from Boston: beaches, ski towns and cities, with fares for Christmas week and New Year's week.
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