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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 26,688 reviews and posted 51 candid photos for Berkshires hotels. Book your Berkshires holiday today!
Or build your own Berkshires holiday package
Build your family-friendly package
Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox
Kids loved the pool (small, about 4'11" deep max, but heated, had lots of pool toys), free lobby cookies, board games, and books. Great morning breakfast. Room clean and...
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Build your luxury package
Hampton Terrace Bed and Breakfast Inn
Hampton Terrace Bed and Breakfast Inn
The Hampton Terrace has become our family's choice to stay in the Berkshires. Attention to detail and pleasing his guests, Stan is the Man! The cozy rooms....the delicious...
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Build your budget package
Willows Motel
Willows Motel
Wonderful owners. Huge breakfast. #5 room has an all-new mattress and bathroom. Big TV. Quiet. Love this little gem. Great location - between the Clark Museum, Williamstown main...
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Cheap Flights to Berkshires
All Washington to Boston (WAS-BOS) fares found by travellers in the past 72 hours*
May
US$103 return
Jun
US$103 return
Jul
US$103 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.