
Cheshire Packages (Flight + Hotel)
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Top hotels in Cheshire

Harbour House Inn
725 North State Road, Cheshire, MA
The price is ฿8,480 per night from 5 Nov to 6 Nov
฿8,480
฿8,964 total
5 Nov - 6 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 ฿2,966 per night from 12 Nov to 13 Nov
฿2,966
฿3,667 total
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 ฿4,648 per night from 24 Nov to 25 Nov
฿4,648
฿5,192 total
24 Nov - 25 Nov
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
Very clean and inviting Hotel located in downtown area. Very walkable area. Parking was free. Front desk very friendly and helpful. Would stay again.
Reviewed on 3 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.
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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.
