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Great Barrington Holiday Packages

Monument Mountain
Great Barrington, Massachussetts
One of the views
Great Barrington Holiday Packages
Want to book a vacation to Great Barrington? Whether you are off for a romantic vacation, family trip, or an all-inclusive holiday, Great Barrington vacation packages on TripAdvisor make planning your trip simple and affordable.
Find the perfect vacation package for Great Barrington on TripAdvisor by comparing Great Barrington hotel and flight prices. Travelers like you have written 3,254 reviews and posted 1,484 candid photos for Great Barrington hotels. Book your Great Barrington vacation today!
Or build your own Great Barrington holiday package
Briarcliff Motel
#1 Hotel in Great Barrington
Briarcliff Motel
We visit the area often and continue to enjoy the mix of old-school Berkshire roadside lodging and modernist touches with which the moteliers have imbued the Briarcliff. Even on a...
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Fairfield Inn & Suites Lenox Great Barrington/Berkshires
#2 Hotel in Great Barrington
Fairfield Inn & Suites Lenox Great Barrington/Berkshires
We were very pleased with our experience from the moment we walked in the door. Service desk employees were very professional and courteous, and they gave us great suggestions for...
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Lantern House Motel Great Barrington
#3 Hotel in Great Barrington
Lantern House Motel Great Barrington
I've stayed at the LHM twice now. It's my go-to place to stay in the Berkshires. It's comfortable, conveniently located (north of Great Barrington center, out of the gridlock) and...
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Cheap Flights to Great Barrington
All Washington to Hartford (WAS-BDL) fares found by travellers in the past 72 hours*
May
US$123 return
Jun
US$123 return
Jul
US$123 return
†  Prices are based on round trip travel with returns between 1-21 days after departure. These are the best fares found by travellers who searched TripAdvisor and a select group of our fare search partners in the past 72 hours. Ticket prices and seat availability change rapidly and cannot be guaranteed.