Chester Holidays
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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! (2,247 reviews)
Ver quiet and clean. Staff was friendly and accommodating
Reviewed on 10 Feb 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is €126 per night from 16 Feb to 17 Feb
€126
16 Feb - 17 Feb
includes taxes & fees
9/10 Wonderful! (839 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 €87 per night from 22 Feb to 23 Feb
€87
22 Feb - 23 Feb
includes taxes & fees
9.2/10 Wonderful! (1,014 reviews)
All of the above plus its consistency. Reliable stay every time.
Reviewed on 11 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.
