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
9/10 Wonderful! (766 reviews)
When we are out in Pittsfield we always stay at the BML. The rooms are spacious, clean, and comfortable. For the price of a hotel room, you get a small condo. The staff is always friendly and helpful. Stay there, you won't regret it.
Reviewed on 26 Nov 2025
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is 2.449.153 ₫ per night from 12 Dec to 13 Dec
2.449.153 ₫
2.735.703 ₫ total
12 Dec - 13 Dec
includes taxes & fees
8/10 Very Good! (971 reviews)
Everything was great.
Reviewed on 24 Nov 2025
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is 2.464.974 ₫ per night from 4 Dec to 5 Dec
2.464.974 ₫
2.753.377 ₫ total
4 Dec - 5 Dec
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
Loved having coffee and tea 24/7
Reviewed on 29 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.
Colonial Theater
You can make plans for a show at Colonial Theater on your trip to Pittsfield. Wander the lakeside in this quaint area.
More trip options
Expedia's Latest Trends
Hotels
Flights
Packages
