
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 €238 per night from 9 Sept to 10 Sept
€238
9 Sept - 10 Sept
includes taxes & fees

Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is €111 per night from 7 Sept to 8 Sept
€111
7 Sept - 8 Sept
includes taxes & fees
8.6/10 Excellent! (1,969 reviews)
"The staff at Vacation Village are simply amazing! Super nice and very helpful. Very clean, lots of amenities, and spacious rooms! Will definitely stay again!"
Reviewed on 24 Aug 2025

Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
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.