Chester Trip
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Top hotels in Chester
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 ₹10,332 per night from 17 Feb to 18 Feb
₹10,332
₹13,565 total
17 Feb - 18 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 ₹8,398 per night from 24 Feb to 25 Feb
₹8,398
₹9,380 total
24 Feb - 25 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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