Pittsfield Holidays

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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.

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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is £89 per night from 26 Apr to 27 Apr
£89
26 Apr - 27 Apr
includes taxes & fees
9/10 Wonderful! (888 reviews)
very clean and friendly staff

Reviewed on 24 Mar 2026

Berkshire Mountain Lodge
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Fully refundable
The price is £107 per night from 8 Apr to 9 Apr
£107
8 Apr - 9 Apr
includes taxes & fees
8/10 Very Good! (1,000 reviews)
Staff was pleasant! Clean and the restaurant was excellent!

Reviewed on 22 Mar 2026

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is £125 per night from 13 Apr to 14 Apr
£125
13 Apr - 14 Apr
includes taxes & fees
9.6/10 Exceptional! (837 reviews)
The hotel was even more beautiful in person! Rooms were incredibly spacious and lovely. The staff was incredibly friendly and helpful. Great stay would definitley return.

Reviewed on 16 Mar 2026

Hotel On North
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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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.