We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

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 27,009 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
We stayed here for 4 nights while vacationing in The Berkshires. The location is perfect! It is right in the middle of everything, so we only had to drive 10-15 minutes in any...
1. Find your perfect hotel
2. Find the right flight
Build your luxury package
Hampton Terrace Bed and Breakfast Inn
Hampton Terrace Bed and Breakfast Inn
“Great stay” 22/05/2017
Our stay in one of the suites was impeccable! On top of everything the other reviewers have mentioned (e.g. facility, breakfast, etc.), Stan generously allowed us a late checking...
1. Find your perfect hotel
2. Find the right flight
Build your budget package
MAPLE TERRACE MOTEL
MAPLE TERRACE MOTEL
I would heartily recommend this motel. The owners very kindly had my room ready for me when I arrived earlier than expected after the drive to Williamstown from New York City. The...
1. Find your perfect hotel
2. Find the right flight
Cheap Flights to Berkshires
All Washington to Boston (WAS-BOS) fares found by travellers in the past 72 hours*
Jun
US$93 round trip
Jul
US$107 round trip
Aug
US$107 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.