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Great Barrington Hotel + Air Packages

Early morning docks
Monument Mountain
Great Barrington, Massachussetts
Build your own Great Barrington vacation package
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 1,885 reviews and posted 637 candid photos for Great Barrington hotels. Book your Great Barrington vacation today!
Briarcliff Motel
#1 Hotel in Great Barrington
Briarcliff Motel
A one-night stay was enough to make me want to return to GB for a return visit to the Briarcliff. The rooms are spacious and airy, large comfortable beds, and charmingly...
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Lantern House Motel Great Barrington
#2 Hotel in Great Barrington
Lantern House Motel Great Barrington
“Big Surprise” 07/20/2014
I was skeptical when Hasu gave me a price of $65 for a room with 2 queen beds for a Thursday night. I had previously called the nearby Holiday Inn Express and Comfort Inn and...
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Monument Mountain Motel
#3 Hotel in Great Barrington
Monument Mountain Motel
Stayed here for two nights during a COLD, snowy February visit to my former home town. The building has been around for at least 50 years, but it has been nicely updated and...
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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*
Aug
$89 round trip
Sep
$89 round trip
Oct
$89 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.