
Pittsfield Holidays from £838
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Your Pittsfield Holiday
When you book a Pittsfield holiday package, you can kick back and enjoy your escape to the fullest. Delve into the highlights of this exciting city knowing that all your travel arrangements have been looked after before you go. A trip to Pittsfield is a wonderful opportunity to sightsee. Be sure to stop by big-name attractions such as Bousquet Ski Area, Colonial Theatre and Hancock Shaker Village. Expedia will help you escape the everyday. Tailor your holiday to Pittsfield to suit your style of travel, whatever that may look like.
Top Pittsfield Flight + Hotel Deals


The Equinox Golf Resort & Spa
Reviewed on 14 Jul 2025


Pittsfield Essential Information
Language | English |
---|---|
Currency | U.S dollars |
Population | 43,300 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 24ºC |
Top Sights | Jiminy Peak Mountain Resort, Norman Rockwell Museum and Bousquet Ski Area |
Top hotels in Pittsfield

Best Western Plus Berkshire Hills Inn & Suites
Reviewed on 13 Jul 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Reviewed on 16 Jul 2025

FairBridge Inn Express
Reviewed on 1 Jul 2025
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.