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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 2,424 reviews and posted 912 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
We stopped over one night en route elsewhere as the motel is easy to access from Interstate 90. This was our first proper US motel and was a pleasant surprise. The rooms are...
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Monument Mountain Motel
#2 Hotel in Great Barrington
Monument Mountain Motel
This is a small well run motel that's convenient to shopping, dining and area attractions. The staff was friendly and attentive. Our room was very clean and comfortable. We had a...
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Fairfield Inn & Suites Lenox Great Barrington/Berkshires
#3 Hotel in Great Barrington
Fairfield Inn & Suites Lenox Great Barrington/Berkshires
I'm normally a Marriott property traveler, was in between Connecticut and New York on this trip and needed a spot to stay. This Fairfield Inn was convenient and I was impressed...
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Cheap Flights to Great Barrington
All Washington to Hartford (WAS-BDL) fares found by travelers in the past 72 hours*
Sep
$87 round trip
Oct
$87 round trip
Nov
$87 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.