Cheshire Holidays
Photo by Ed Gaffny
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Top hotels in Cheshire
Harbour House Inn
725 North State Road Cheshire MA
The price is €239 per night from 11 Dec to 12 Dec
€239
11 Dec - 12 Dec
includes taxes & fees
9.6/10 Exceptional! (39 reviews)
Great place, great hosts, lovely experience. Would go back 100x.
Reviewed on 14 Nov 2025
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is €81 per night from 29 Nov to 30 Nov
€81
29 Nov - 30 Nov
includes taxes & fees
8.6/10 Excellent! (2,146 reviews)
Nice place to stay, off season. Price was very reasonable. Room was comfortable, (1st floor, Building 5), entire building was very quiet, hardly anyone on the property. Nice amenities, but we only walked through, did not use (pool, locker rooms, hot tub, fire pit). Room was nicely appointed and comfortable. ...
Reviewed on 22 Nov 2025
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
The price is €103 per night from 20 Dec to 21 Dec
€103
20 Dec - 21 Dec
includes taxes & fees
8.6/10 Excellent! (1,008 reviews)
Wonderful Experience
Reviewed on 23 Nov 2025
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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