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
9/10 Wonderful! (763 reviews)
The room was very clean, appreciated the friendly and helpful staff. Well stocked kitchen, super close to grocery stores and restaurants.
Reviewed on 21 Nov 2025
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is 2.355.206 ₫ per night from 29 Nov to 30 Nov
2.355.206 ₫
2.630.765 ₫ total
29 Nov - 30 Nov
includes taxes & fees
7.8/10 Good! (962 reviews)
Great location! Lovely staff!
Reviewed on 18 Nov 2025
Hotel On North
297 North Street Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is 3.516.408 ₫ per night from 22 Dec to 23 Dec
3.516.408 ₫
3.927.827 ₫ total
22 Dec - 23 Dec
includes taxes & fees
9.4/10 Exceptional! (798 reviews)
The room was very clean and spacious ! The staff were very friendly and helpful - the hotel itself had a great vibe complete with hardcover books in a little coffee nook - just perfect and fun !
Reviewed on 10 Nov 2025
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.
Popular places to visit
Bousquet Ski Area
Hit the slopes at Bousquet Ski Area during your trip to Pittsfield. Wander the lakeside in this quaint area.
Berkshire Museum
You can spend an afternoon studying the exhibits at Berkshire Museum in Pittsfield. Wander the lakeside in this family-friendly area.
Hancock Shaker Village
5/5(2 reviews)
You can browse the exhibits at Hancock Shaker Village, a museum with a story of its own, during your travels to Pittsfield. Wander the lakeside in this quaint area.
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