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 6.917.113 ₫ per night from 3 Dec to 4 Dec
6.917.113 ₫
7.311.389 ₫ total
3 Dec - 4 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 1.952.826 ₫ per night from 29 Nov to 30 Nov
1.952.826 ₫
2.470.596 ₫ total
29 Nov - 30 Nov
includes taxes & fees
8.6/10 Excellent! (2,136 reviews)
Clean beautiful place
Reviewed on 18 Nov 2025
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
The price is 2.824.334 ₫ per night from 20 Dec to 21 Dec
2.824.334 ₫
3.154.781 ₫ total
20 Dec - 21 Dec
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
All the design elements are wonderful! I enjoyed the room and the beautiful view of the town and the mountains. So clean and so spacious!! The staff - not so much, but everything else great.
Reviewed on 20 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.
