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
The price is S$153 per night from 8 Feb to 9 Feb
S$153
8 Feb - 9 Feb
includes taxes & fees
9.2/10 Wonderful! (2,237 reviews)
YES
Reviewed on 5 Feb, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is S$169 per night from 8 Feb to 9 Feb
S$169
8 Feb - 9 Feb
includes taxes & fees
9/10 Wonderful! (828 reviews)
Only stayed for 1 night but was very impressed with this property. The room was very clean and spacious. Bed was comfortable as well. Had my two kids with me so the pool and hot tub was an amazing amenity. Left early in the morning to ski so the stay was short, but would’ve loved to stay longer and ...
Reviewed on 5 Feb, 2026
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is S$139 per night from 11 Feb to 12 Feb
S$139
11 Feb - 12 Feb
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
The staff is very helpful, and always willing to assist with any inquiries. The room was definitely clean and well-stocked throughout our entire stay.
Reviewed on 5 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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