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 S$346 per night from 1 Dec to 2 Dec
S$346
1 Dec - 2 Dec
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 S$148 per night from 12 Nov to 13 Nov
S$148
12 Nov - 13 Nov
includes taxes & fees
8.6/10 Excellent! (2,117 reviews)
The amenities are great. The pool and hot tub are very comfortable temperatures, pool tables, ping pong, foosball, arcade games, movie theater, and more.
Reviewed on 2 Nov, 2025
Hotel Downstreet, an Ascend Collection Hotel
40 Main St, North Adams, MA
Fully refundable
The price is S$209 per night from 9 Dec to 10 Dec
S$209
9 Dec - 10 Dec
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
Kind staff!
Reviewed on 28 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
