
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 25 Aug to 26 Aug
€238
25 Aug - 26 Aug
includes taxes & fees
9.6/10 Exceptional! (37 reviews)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!!"
Reviewed on 4 Jul 2025

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! (1,952 reviews)
"Liked the fact there are 2 pools, an indoor and an outdoor."
Reviewed on 17 Aug 2025

Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is €82 per night from 7 Sept to 8 Sept
€82
7 Sept - 8 Sept
includes taxes & fees
8.8/10 Excellent! (582 reviews)
"Enjoyed the room, towels and kitchen. I can recommend."
Reviewed on 18 Aug 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.