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

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 26,002 reviews and posted 49 candid photos for Berkshires hotels. Book your Berkshires holiday today!
Or build your own Berkshires holiday package
Hotel on North
#1 Hotel in Berkshires
Hotel on North
This was by far one of the best hotel experiences I have ever had and I have traveled a ton both domestically and abroad. Exceptional in every way, the Hotel on North is a lovely...
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Hampton Terrace Inn
#2 Hotel in Berkshires
Hampton Terrace Inn
Although located in a 1897 house, you get all the modern utilities that you require in a hotel. The host was very kind, friendly and helpful, providing from the beginning all the...
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LakeHouse Inn
#3 Hotel in Berkshires
LakeHouse Inn
My husband and I stayed here one weekend night in mid-November. The inn has been beautifully renovated keeping the classic charm of a 100+ year old inn with modern amenities...
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Cheap Flights to Berkshires
All Washington to Boston (WAS-BOS) fares found by travellers in the past 72 hours*
Dec
USD 80 return
Jan
USD 81 return
Feb
USD 81 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.