Pittsfield Holidays
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Top hotels in Pittsfield
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is S$153 per night from 24 May to 25 May
S$153
24 May - 25 May
includes taxes & fees
9/10 Wonderful! (925 reviews)
Room very spacious and clean. Full kitchen is a great bonus.
Reviewed on 4 May, 2026
Hotel On North
297 North Street Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is S$211 per night from 12 May to 13 May
S$211
12 May - 13 May
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 8 May, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Fully refundable
The price is S$167 per night from 17 May to 18 May
S$167
17 May - 18 May
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 19 Apr, 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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