Chesterfield Packages (Flight + Hotel)
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Top hotels in Chesterfield
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (2,224 reviews)
We have stayed here before. We like the location it’s off the beaten path a bit. Staff is lovely, breakfast is great. We wish they had pillow options as their pillows are just too big and our necks can’t handle it. We reached out and admin said they would consider having pilllow options in the future. ...
Reviewed on 13 Feb 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is ฿3,542 per night from 17 Feb to 18 Feb
฿3,542
฿4,651 total
17 Feb - 18 Feb
includes taxes & fees
9/10 Wonderful! (838 reviews)
Perfect location, big rooms, nice staff.
Reviewed on 10 Feb 2026
Comfort Inn & Suites
400 Russell St Hadley MA
Fully refundableReserve now, pay when you stay
The price is ฿3,505 per night from 8 Mar to 9 Mar
฿3,505
฿3,915 total
8 Mar - 9 Mar
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
Yes, on all counts!
Reviewed on 16 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
