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Great Barrington Vacation Packages

Early morning docks
Monument Mountain
Great Barrington, Massachussetts
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 2,108 reviews and posted 707 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
I love old roadside hotels and the proprietors of the Briarcliff have reclaimed, repurposed, and renovated this quintessentially American structure to be a sophisticated...
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Lantern House Motel Great Barrington
#2 Hotel in Great Barrington
Lantern House Motel Great Barrington
Large clean room, clean bathroom, good quality sheets (not thin and pilled like in some places) and towels. Rooms have microwave and fridge. Very friendly and helpful owner...
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Fairfield Inn & Suites Lenox Great Barrington/Berkshires
#3 Hotel in Great Barrington
Fairfield Inn & Suites Lenox Great Barrington/Berkshires
Sadly only had 1 nights stay here but enjoyed every minute our Room was very nice as was all the staff we met and the pool was lovely and warm. I think we will have to stay here...
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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
$101 round trip
Jan
$107 round trip
Feb
$101 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.