Chester Holidays
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Chester Holiday
Our pick of the best Chester Hotel Deals
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (2,245 reviews)
Staff was very nice, room was clean. Breakfast was good.
Reviewed on 9 Feb 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is NZ$247 per night from 19 Feb to 20 Feb
NZ$247
19 Feb - 20 Feb
includes taxes & fees
9/10 Wonderful! (838 reviews)
Perfect location, big rooms, nice staff.
Reviewed on 10 Feb 2026
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is NZ$171 per night from 22 Feb to 23 Feb
NZ$171
22 Feb - 23 Feb
includes taxes & fees
9/10 Wonderful! (1,013 reviews)
Traveling during freezing temperatures was a challenge but once we arrived at the Yankee Inn, we felt welcome and comfortable. Pre check-in was easy and our room was clean and warm and cozy. We ordered in and were told there were tables on the 2nd floor outside the breakfast room where we could eat ...
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.
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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.
