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 349 per night from Sep 15 to Sep 16
AED 349
AED 431 total
15 Sep - 16 Sep
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 ...
Vacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
The price is AED 526 per night from Sep 27 to Sep 28
AED 526
AED 588 total
27 Sep - 28 Sep
includes taxes & fees
Book a stay at this business-friendly hotel in North Adams. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Hotel Downstreet, an Ascend Collection Hotel
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is AED 292 per night from Oct 1 to Oct 2
AED 292
AED 409 total
1 Oct - 2 Oct
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! (1,122 reviews)
"Clean room nice Kitchenette with everything."

Reviewed on 4 September 2026

Berkshire Mountain Lodge
See all 1,010 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.
Berkshire's Family Gathering & Mountain Escape!

Berkshire's Family Gathering & Mountain Escape!

Cheshire MA
Book a stay at this family-friendly vacation home in Cheshire. Enjoy laundry facilities, a pool table, and patios. Popular attractions Susan B. Anthony Birthplace ...
Berkshire's Family Gathering & Mountain Escape!
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 ...
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! (1,122 reviews)
"Clean room nice Kitchenette with everything."

Reviewed on 4 September 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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