Cheshire, MA

Travel Guide

A lake surrounded by autumn-colored trees and hills.
A lake with lily pads and reeds, surrounded by autumn-colored trees and hills.
A lake surrounded by autumn-colored trees with a clear sky.
A rural road with a double yellow line, surrounded by green fields and trees, under a partly cloudy sky.
A frozen lake with a group of ducks swimming in the center.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
The price is AED 295 per night from Nov 8 to Nov 9
AED 295
AED 370 total
8 Nov - 9 Nov
includes taxes & fees
Book a stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (2,830 reviews)
"Great"

Reviewed on 5 November 2026

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is AED 282 per night from Dec 6 to Dec 7
AED 282
AED 397 total
6 Dec - 7 Dec
includes taxes & fees
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,257 reviews)
"Very centrally located. Right next to a good little market. Very reasonable price for an apartment like room."

Reviewed on 5 November 2026

Berkshire Mountain Lodge
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is AED 415 per night from Nov 20 to Nov 21
AED 415
AED 464 total
20 Nov - 21 Nov
includes taxes & fees
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
The Yankee Inn
See all 982 properties in Cheshire
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.
19th c. Barn in the Berkshires

19th c. Barn in the Berkshires

Cheshire MA
Stay at this vacation home in Cheshire. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Jiminy Peak Mountain Resort and Cheshire Reservoir ...
9.6/10 Exceptional! (101 reviews)
"This is a special spot for our family. We've stayed here twice and look forward to our next visit!"

Reviewed on 13 September 2026

19th c. Barn in the Berkshires
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Book a stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (2,830 reviews)
"Great"

Reviewed on 5 November 2026

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,257 reviews)
"Very centrally located. Right next to a good little market. Very reasonable price for an apartment like room."

Reviewed on 5 November 2026

Berkshire Mountain Lodge
See all properties in Cheshire
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.

Stay near popular Cheshire attractions

St Mary's of the Assumption Church

10.0/10 (1 review)
St Mary's of the Assumption Church is just one of the places to see in Cheshire, so why not enjoy the other things to explore during your travels? Discover the area's mountain views, or seek out its ski slopes.
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