Cheshire Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Ed Gaffny
Top hotels in Cheshire
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is 2.730.721 ₫ per night from 8 Feb to 9 Feb
2.730.721 ₫
3.338.331 ₫ total
8 Feb - 9 Feb
includes taxes & fees
8.6/10 Excellent! (2,205 reviews)
The amount of space and super comfortable bed was such a pleasure!
Reviewed on 13 Jan 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is 2.591.863 ₫ per night from 3 Feb to 4 Feb
2.591.863 ₫
3.481.850 ₫ total
3 Feb - 4 Feb
includes taxes & fees
9/10 Wonderful! (814 reviews)
There needs to be an adult only hot tub. Both days we used, other kids had it taken over.
Reviewed on 18 Jan 2026
The Williams Inn
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
The price is 4.889.044 ₫ per night from 28 Jan to 29 Jan
4.889.044 ₫
5.461.063 ₫ total
28 Jan - 29 Jan
includes taxes & fees
9.6/10 Exceptional! (560 reviews)
General ambience is lovely.
Reviewed on 8 Jan 2026
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.
