Chesterfield Holidays
Book a Hotel + Flight or Car together to unlock savings
Top hotels in Chesterfield
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (750 reviews)
Everything was so perfect for a weekend to just get away and decompress, the staff were great, the room was awesome.
Reviewed on 4 Nov 2025
Quality Inn West Springfield
1150 Riverdale St, West Springfield, MA
Fully refundableReserve now, pay when you stay
The price is 2.213.692 ₫ per night from 7 Dec to 8 Dec
2.213.692 ₫
2.533.571 ₫ total
7 Dec - 8 Dec
includes taxes & fees
7/10 Good! (1,004 reviews)
The owner makes me feel like I am a personal friend of his and the best part of his day is when I walk in the door.
Reviewed on 7 Nov 2025
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is 2.437.454 ₫ per night from 18 Nov to 19 Nov
2.437.454 ₫
2.722.636 ₫ total
18 Nov - 19 Nov
includes taxes & fees
7.8/10 Good! (946 reviews)
Great stay! Nice quiet room for 2 little “alert “ to outside noise pups!! Comfy beds and central location for the day trips we had planned.
Reviewed on 8 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.
