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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 2,385 reviews and posted 900 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
The Briarcliff is our go-to, short-stay home in the Berkshires. Incredibly convenient located between Stockbridge and Great Barrington and near Tanglewood, the Briarcliff is a fun...
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Monument Mountain Motel
#2 Hotel in Great Barrington
Monument Mountain Motel
We went for a day trip to Mass..naturally the car broke down on a sunday at 4:30pm. He gave us 2 rooms becasue we had the DOG. We tried the pool this time and it was warm and...
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Lantern House Motel Great Barrington
#3 Hotel in Great Barrington
Lantern House Motel Great Barrington
With daughters having studied at the Tanglewood music program over the years, we stayed at the Lantern House a number of times over a 20 year period, but not for the last few...
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Cheap Flights to Great Barrington
All Washington to Hartford (WAS-BDL) fares found by travelers in the past 72 hours*
Aug
$83 round trip
Sep
$83 round trip
Oct
$83 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.