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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 2,309 reviews and posted 831 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 an absolute gem in the Berkshire woods. My week's vacation in the Berkshires began with a bit of a hiccup when I missed my plane on a Monday morning and wasn't...
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Monument Mountain Motel
#2 Hotel in Great Barrington
Monument Mountain Motel
Very much enjoyed this spot - simple, very clean, especially the remodeled bathroom. A real key and windows that open so you can enjoy the breeze. The staff was pleasant and...
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Lantern House Motel Great Barrington
#3 Hotel in Great Barrington
Lantern House Motel Great Barrington
“Wedding Stay” 06/23/2015
We recently stayed at the Lantern House, for a weekend family wedding. We were very pleased with the accommodations and the management! I would recommend staying here to anyone...
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2. Find the right flight
Cheap Flights to Great Barrington
All Washington to Hartford (WAS-BDL) fares found by travelers in the past 72 hours*
Jul
$83 round trip
Aug
$83 round trip
Sep
$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.