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Berkshires Vacation Packages

Monument Mountain
Garden View
About a dozen geese landed in the lake.
Berkshires Vacation Packages
Want to book a vacation to Berkshires? Whether you're off for a romantic vacation, family trip, or an all-inclusive holiday, Berkshires vacation packages on TripAdvisor make planning your trip simple and affordable.
Find the perfect vacation package for Berkshires on TripAdvisor by comparing Berkshires hotel and flight prices. Travelers like you have written 17,069 reviews and posted 28 candid photos for Berkshires hotels. Book your Berkshires vacation today!
Or build your own Berkshires vacation package
Blantyre
#1 Hotel in Berkshires
Blantyre
It felt like we were going to visit a favorite rich uncle or an episode in Downton Abbey. From the written correspondence prior to the visit to the personal attention at arrival...
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Canyon Ranch in Lenox
#2 Hotel in Berkshires
Canyon Ranch in Lenox
This was our 9th annual trip to Canyon a Ranch. Each year we are excited to see the changes. The Ranch is up to date on all of the newest health, exercise and foods, including...
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Briarcliff Motel
#3 Hotel in Berkshires
Briarcliff Motel
The B&B is a wonderful escape. Well positioned between Stockbridge and Great Barrington, the hotel offers a great view of Monument Mountain with a fun hiking trail; virtually...
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Cheap Flights to Berkshires
All Washington to Boston (WAS-BOS) fares found by travelers in the past 72 hours*
Jan
$99 round trip
Feb
$118 round trip
Mar
$137 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.