Pittsfield Holidays
Book a Hotel + Flight or Car together to unlock savings
Top hotels in Pittsfield
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is 2.960.077 ₫ per night from 24 Feb to 25 Feb
2.960.077 ₫
3.886.553 ₫ total
24 Feb - 25 Feb
includes taxes & fees
9/10 Wonderful! (859 reviews)
Second stay. Great as usual!
Reviewed on 22 Feb 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Fully refundable
The price is 2.674.807 ₫ per night from 24 Feb to 25 Feb
2.674.807 ₫
2.987.759 ₫ total
24 Feb - 25 Feb
includes taxes & fees
8/10 Very Good! (1,002 reviews)
Room was nice and tidy. The staff were friendly. Check-in was quick and simple. Breakfast was plenty with eggs, bacon, sausages, waffles and French toast. There was only 1 working elevator so the wait was slow. Parking was undergoing renovation so you need to park down the slope and walk up. There's ...
Reviewed on 22 Feb 2026
Hotel On North
297 North Street Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is 3.869.381 ₫ per night from 26 Feb to 27 Feb
3.869.381 ₫
4.322.021 ₫ total
26 Feb - 27 Feb
includes taxes & fees
9.6/10 Exceptional! (825 reviews)
Room was spotless, staff was amazing! Loved the bathroom setup! Will recommend and stay again!
Reviewed on 9 Feb 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.
Popular places to visit
Bousquet Ski Area
Hit the slopes at Bousquet Ski Area during your trip to 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.
Berkshire Museum
You can spend an afternoon studying the exhibits at Berkshire Museum in Pittsfield. Wander the lakeside in this family-friendly area.
