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New! Find and book your ideal hotel on TripAdvisor — and get the lowest prices

Berkshires Vacation Packages

Monument Mountain
The tower
Garden View
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 25,028 reviews and posted 53 candid photos for Berkshires hotels. Book your Berkshires vacation today!
Or build your own Berkshires vacation package
Hotel on North
#1 Hotel in Berkshires
Hotel on North
Very unique experience. Art studio looks. Spacious bathroom. Tall ceilings. Welcoming staff. In downtown close to restaurants. Would visit again! Quibbles: floor was slippery...
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Canyon Ranch in Lenox
#2 Hotel in Berkshires
Canyon Ranch in Lenox
Fabulous get away. Wonderful lectures.good workout choices and good spa treatments. Be prepared to learn a lot! I highly recommend a visit. The food is excellent and the choices...
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Hampton Inn & Suites Berkshires-Lenox
#3 Hotel in Berkshires
Hampton Inn & Suites Berkshires-Lenox
Nice hotel with a beautiful yard. Easy check in. Clean comfortable room, though a little small. Kitchen lady worked hard to make sure breakfast was enjoyable. Able to use good...
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Cheap Flights to Berkshires
All Washington to Boston (WAS-BOS) fares found by travelers in the past 72 hours*
Oct
$39 round trip
Nov
$39 round trip
Dec
$79 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.