Pittsfield Holidays
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Pittsfield Holiday
Our pick of the best Pittsfield Hotel Deals
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is NZ$267 per night from 15 June to 16 June
NZ$267
15 June - 16 June
includes taxes & fees
9/10 Wonderful! (961 reviews)
"Water pressure in shower overwhelmingly strong"
Reviewed on 2 June 2026
Hotel On North
297 North Street Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is NZ$281 per night from 7 June to 8 June
NZ$281
7 June - 8 June
includes taxes & fees
9.6/10 Exceptional! (864 reviews)
"Hotels Amazing stay here"
Reviewed on 29 May 2026
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
1055 South Street Pittsfield MA
Fully refundable
The price is NZ$249 per night from 7 June to 8 June
NZ$249
7 June - 8 June
includes taxes & fees
9.4/10 Exceptional! (100 reviews)
"I spilled an ENTIRE cup of cocoa I was making for my niece. The clerk on was a very kind, friendly young man named Paul. I have worked as a chef for 30 years, the cocoa went EVERYWHERE. He got a mop bucket , I started cleaning my mess up I just know what its like to walk into a mess!! Left by someone ..."
Reviewed on 1 June 2026
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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- Visit Cheshire
- Visit The Berkshires
- Visit Great Barrington
- Visit West Stockbridge
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- National Shrine of the Divine Mercy
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- Williams College
- Norman Rockwell Museum
- Hadley Farm Museum
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
