Cheshire Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Ed Gaffny
Top hotels in Cheshire
Harbour House Inn
725 North State Road, Cheshire, MA
The price is 6.911.867 ₫ per night from 10 Nov to 11 Nov
6.911.867 ₫
7.305.814 ₫ total
10 Nov - 11 Nov
includes taxes & fees
9.6/10 Exceptional! (38 reviews)
"The owner Brandi was outstanding, friendly, she made us fresh homemade breakfast each morning, which the best. Will differently stay there again. Wonderful place and people."
Reviewed on 12 Sept 2025
Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is 2.418.137 ₫ per night from 2 Nov to 3 Nov
2.418.137 ₫
2.990.250 ₫ total
2 Nov - 3 Nov
includes taxes & fees
8.6/10 Excellent! (2,039 reviews)
"There were a couple of issues withy stay 10/4/26 to 10/5/26. The staff did not answer my text messages sent as they said they were very busy. The room has small insects and flies. It was reported and staff offered to send maintenance to check on the unit. I was moved to another unit 10/5/25 through ..."
Reviewed on 7 Oct 2025
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is 2.023.415 ₫ per night from 2 Nov to 3 Nov
2.023.415 ₫
2.849.081 ₫ total
2 Nov - 3 Nov
includes taxes & fees
8.8/10 Excellent! (678 reviews)
"Great lodge with 1 bedroom suites and fully stocked kitchens"
Reviewed on 7 Oct 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.
