Chester Holidays
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Top hotels in Chester
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is S$153 per night from 24 May to 25 May
S$153
24 May - 25 May
includes taxes & fees
9/10 Wonderful! (925 reviews)
Room very spacious and clean. Full kitchen is a great bonus.
Reviewed on 4 May, 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is S$138 per night from 11 May to 12 May
S$138
11 May - 12 May
includes taxes & fees
9/10 Wonderful! (932 reviews)
Easy, comfortable and convenient; rooms and public spaces are nice, modern and stylish updates of modest 60s/70s original motel facilities.
Reviewed on 6 May, 2026
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
The price is S$251 per night from 17 May to 18 May
S$251
17 May - 18 May
includes taxes & fees
9.2/10 Wonderful! (2,219 reviews)
The room was massive and roomy. The floor was shiny and clean. Everything was tidy. The bed and pillows were comfortable.
Reviewed on 6 May, 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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