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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 2,230 reviews and posted 763 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
Had a really great stay at The Briarcliff. The owners took what was undoubtedly a run down 1960s era strip motel, modernized it and made it really cool and interesting...
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Lantern House Motel Great Barrington
#2 Hotel in Great Barrington
Lantern House Motel Great Barrington
Ordinarily I'd be leery of a one-story motel where you park your car right outside the door to your room. But this place is clean, modern and easy, and has to be the greatest deal...
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Monument Mountain Motel
#3 Hotel in Great Barrington
Monument Mountain Motel
The hotel is very unassuming from the outside. It was March and very cold so the pool was not an option . The room was immaculate and very warm and comfortable. There is a...
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Cheap Flights to Great Barrington
All Washington to Hartford (WAS-BDL) fares found by travelers in the past 72 hours*
Apr
$68 round trip
May
find price round trip
Jun
$68 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.