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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 1,981 reviews and posted 656 candid photos for Great Barrington hotels. Book your Great Barrington vacation today!
Briarcliff Motel
#1 Hotel in Great Barrington
Briarcliff Motel
The Briarcliff has just had a facelift and she is beautiful. The couple that own and run Briarcliff and delightful and very easy to talk to. Samantha, checked us in and was also...
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Lantern House Motel Great Barrington
#2 Hotel in Great Barrington
Lantern House Motel Great Barrington
The family owned establishment of the lantern house is our end of the summer getaway, perfect spot for our weekend of racing. Clean, comfy, quaint... always a pleasant stay...
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Monument Mountain Motel
#3 Hotel in Great Barrington
Monument Mountain Motel
Clean, modest accommodations in the heart of the Berkshires. I agree with all the other positive reviews. Mid-week rates are great! They go up beginning on Friday night. Small...
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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*
Sep
$83 round trip
Oct
$77 round trip
Nov
$77 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.