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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 3,135 reviews and posted 1,340 candid photos for Great Barrington hotels. Book your Great Barrington vacation today!
Or build your own Great Barrington vacation package
Briarcliff Motel
#1 Hotel in Great Barrington
Briarcliff Motel
We spend every winter weekend at the Briarcliff because of the easy access to Butternut. We're big fans. The breakfast is wonderful. The rooms are clean and comfortable. The...
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Fairfield Inn & Suites Lenox Great Barrington/Berkshires
#2 Hotel in Great Barrington
Fairfield Inn & Suites Lenox Great Barrington/Berkshires
My sister and I spent a night here for a girls night away from our busy lives in NY. We enjoyed the pool and whirlpool. There was only one other person sharing it with us and we...
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Days Inn Great Barrington
#3 Hotel in Great Barrington
Days Inn Great Barrington
We spent a couple of nights here and everything was just fine; no issues at all. Convenient, reasonable, clean and comfortable.
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Cheap Flights to Great Barrington
All Washington to Hartford (WAS-BDL) fares found by travelers in the past 72 hours*
Feb
$77 round trip
Mar
$107 round trip
Apr
$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.