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Berkshires Vacation Packages

Monument Mountain
The tower
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 27,894 reviews and posted 51 candid photos for Berkshires hotels. Book your Berkshires vacation today!
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Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox
The Hampton Inn and Suites was ideally located to visit Historic Lenox, Tanglewood, and Stockbridge. The staff is friendly and helpful. The guest rooms are comfortable and clean...
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Build your luxury package
LakeHouse Inn
LakeHouse Inn
Location. Location. Location. We came to the Berkshires to hike, bike, listen to music and visit museums. We did all that AND spent from 4-8pm everyday kayaking, swimming and...
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Build your budget package
Mountain View Motel
Mountain View Motel
“Nice stay” 07/19/2017
The family who owns the motel is very very nice. My boyfriend and I had a very great stay and although the outside could use some updating, the inside is very clean and looks like...
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Cheap Flights to Berkshires
All Washington to Boston (WAS-BOS) fares found by travelers in the past 72 hours*
Aug
$97 round trip
Sep
$97 round trip
Oct
$97 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.