Cheshire Holidays
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Cheshire Holiday
Our pick of the best Cheshire Hotel Deals
Harbour House Inn
725 North State Road, Cheshire, MA
The price is NZ$473 per night from 25 Nov to 26 Nov
NZ$473
25 Nov - 26 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 NZ$202 per night from 12 Nov to 13 Nov
NZ$202
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 NZ$285 per night from 9 Dec to 10 Dec
NZ$285
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.
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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.
