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Berkshires Holiday Packages

Monument Mountain
The tower
Garden View
Berkshires Holiday Packages
Want to book a holiday to Berkshires? Whether you're off for a romantic holiday, family trip, or an all-inclusive holiday, Berkshires holiday packages on TripAdvisor make planning your trip simple and affordable.
Find the perfect holiday package for Berkshires on TripAdvisor by comparing Berkshires hotel and flight prices. Travellers like you have written 27,452 reviews and posted 51 candid photos for Berkshires hotels. Book your Berkshires holiday today!
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Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox
Incredible place. Love this hotel. Clean, friendly, bright and a perfect place to get away and hide away for a week or more. We have spent the last 8 wedding anniversaries at this...
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Build your luxury package
LakeHouse Inn
LakeHouse Inn
This beautifully renovated lake front inn was a real treat. The staff was friendly and helpful, the breakfast was delicious, and the ground were gorgeous. Great mix of an old...
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Build your budget package
Mountain View Motel
Mountain View Motel
Stayed for one night to play a gig at Castle Street. Good location close enough to the center of Great Barrington.The room was larger than expected with a couch, table and...
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Cheap Flights to Berkshires
All Washington to Boston (WAS-BOS) fares found by travellers in the past 72 hours*
Jul
US$103 round trip
Aug
US$97 round trip
Sep
US$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 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.