Pittsfield Vacations
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Find the Best Pittsfield Vacation Packages
Pittsfield Hotel Deals
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is ￥13,763 per night from May 24 to May 25
￥13,763
￥18,878 total
May 24 - May 25
includes taxes & fees
9/10 Wonderful! (925 reviews)
Room very spacious and clean. Full kitchen is a great bonus.
Reviewed on May 4, 2026
Hotel On North
297 North Street Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is ￥23,345 per night from May 12 to May 13
￥23,345
￥26,077 total
May 12 - May 13
includes taxes & fees
9.6/10 Exceptional! (848 reviews)
Lovely “old” hotel, used to be a men’s clothing store, but it has been remodelled into an exceptional place to stay in downtown Pittsfield. Our room was huge, clean, comfy beds, nice sitting area, desk area, coffee/tea area, and shelves of books! The bathroom was huge, clean, and well-supplied. There ...
Reviewed on May 8, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Fully refundable
The price is ￥18,488 per night from May 17 to May 18
￥18,488
￥20,652 total
May 17 - May 18
includes taxes & fees
8/10 Very Good! (1,003 reviews)
Staff was nice. Room was clean. Parking lot was under construction. Had to park offsite. Wasn't a total inconvenience. One elevator was broken and the wait time was long each time we were trying to use.
Reviewed on Apr 19, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
