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Great Barrington Vacation Packages

Monument Mountain
Great Barrington, Massachussetts
One of the views
Great Barrington Vacation Packages
Want to book a vacation to Great Barrington? Whether you're 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 3,092 reviews and posted 1,319 candid photos for Great Barrington hotels. Book your Great Barrington vacation today!
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Briarcliff Motel
#1 Hotel in Great Barrington
Briarcliff Motel
“September” 11/09/2016
As members of the Ford-V8 Antique Club we went to the Berkshires to find a Motel that we could stay for a weekend and enjoy the sites. We came upon the Briarcliff and we all fell...
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Fairfield Inn & Suites Lenox Great Barrington/Berkshires
#2 Hotel in Great Barrington
Fairfield Inn & Suites Lenox Great Barrington/Berkshires
Very friendly staff. Got our room immediately. Clean room with fridge microwave coffee maker. Breakfast had eggs waffles bacon sausage cereals bagels pastries fruit and a few...
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Days Inn Great Barrington
#3 Hotel in Great Barrington
Days Inn Great Barrington
This hotel could use a total makeover, but it was the ideal location for a family get together. The hotel had easy access to skiing, and there are some great homes to rent for a...
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Cheap Flights to Great Barrington
All Washington to Hartford (WAS-BDL) fares found by travelers in the past 72 hours*
Dec
$107 round trip
Jan
$107 round trip
Feb
$107 round trip
†  Prices are based on round trip travel with returns between 1-21 days after departure. These are the best fares found by travelers 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.