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Great Barrington Holiday Packages

Monument Mountain
Great Barrington, Massachussetts
One of the views
Great Barrington Holiday Packages
Want to book a holiday to Great Barrington? Whether you're off for a romantic holiday, family trip, or an all-inclusive holiday, Great Barrington holiday packages on TripAdvisor make planning your trip simple and affordable.
Find the perfect holiday package for Great Barrington on TripAdvisor by comparing Great Barrington hotel and flight prices. Travellers like you have written 3,340 reviews and posted 1,502 candid photos for Great Barrington hotels. Book your Great Barrington holiday today!
Or build your own Great Barrington holiday package
Briarcliff Motel
#1 Hotel in Great Barrington
Briarcliff Motel
Our family (two teens) of four spent two evenings at the Briarcliff. The motel is lovely, and the owners have put real thought into the updated and functional design of the rooms...
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2. Find the right flight
Fairfield Inn & Suites Lenox Great Barrington/Berkshires
#2 Hotel in Great Barrington
Fairfield Inn & Suites Lenox Great Barrington/Berkshires
We decided to take a trip to the Berkshires for our 50th wedding anniversary last week, and we chose the Fairfield Inn in Great Barrington, MA. I always read reviews of any hotel...
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Lantern House Motel Great Barrington
#3 Hotel in Great Barrington
Lantern House Motel Great Barrington
I was very pleasantly surprised. Our late check in was kindly accommodated, the room was not only spotlessly clean but was newly furnished, and the grounds are lovely and well...
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2. Find the right flight
Cheap Flights to Great Barrington
All Washington to Hartford (WAS-BDL) fares found by travellers in the past 72 hours*
Jul
US$129 return
Aug
US$129 return
Sep
US$129 return
†  Prices are based on round trip travel with returns between 1-21 days after departure. These are the best fares found by travellers 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.