Chesterfield Holidays
Book a Hotel + Flight or Car together to unlock savings
Top hotels in Chesterfield
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
The price is 2.874.415 ₫ per night from 4 Jan to 5 Jan
2.874.415 ₫
3.339.124 ₫ total
4 Jan - 5 Jan 2026
includes taxes & fees
9.2/10 Wonderful! (2,257 reviews)
A great check-in experience
Reviewed on 16 Dec 2025
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Fully refundable
The price is 2.473.328 ₫ per night from 19 Dec to 20 Dec
2.473.328 ₫
2.762.708 ₫ total
19 Dec - 20 Dec
includes taxes & fees
8/10 Very Good! (988 reviews)
Very clean and timely and efficient and the lady who checked me in named Valerie did an amazing job and was very informative and helpful .
Reviewed on 15 Dec 2025
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is 2.596.600 ₫ per night from 8 Jan to 9 Jan
2.596.600 ₫
3.488.212 ₫ total
8 Jan - 9 Jan 2026
includes taxes & fees
9/10 Wonderful! (788 reviews)
Nice room
Reviewed on 9 Dec 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.
