Cheshire, MA

Travel Guide

Photo by Ed Gaffny
Photo by Ed Gaffny
Photo by Chris Addams
Photo by Chris Addams
Photo by Chris Addams
Photo by Chris Addams
Photo by Chris Addams
Photo by Chris Addams
Photo by Chris Addams
Photo by Chris Addams
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is SAR 406 per night from Sep 14 to Sep 15
SAR 406
SAR 495 total
14 Sep - 15 Sep
includes taxes & fees
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,911 reviews)
"Room was very clean. There is a lot to do at the property, 2 pools, activities for the kids. Lots of things to do in the area"

Reviewed on 28 August 2025

Vacation Village in the Berkshires
Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

3 out of 5
40 Main St, North Adams, MA
The price is SAR 564 per night from Oct 1 to Oct 2
SAR 564
SAR 630 total
1 Oct - 2 Oct
includes taxes & fees
Stay at this 3-star hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
Hotel Downstreet, Ascend Hotel Collection
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
The price is SAR 370 per night from Oct 1 to Oct 2
SAR 370
SAR 497 total
1 Oct - 2 Oct
includes taxes & fees
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
Berkshire Mountain Lodge
See all 987 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.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,911 reviews)
"Room was very clean. There is a lot to do at the property, 2 pools, activities for the kids. Lots of things to do in the area"

Reviewed on 28 August 2025

Vacation Village in the Berkshires
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3 out of 5
37 Corey Rd, Hancock, MA
Stay at this 3-star ski condo in Hancock. Enjoy free parking, 2 restaurants, and 2 hot tubs. Our guests praise the property condition in our reviews. Popular ...
Jiminy Peak Mountain Resort
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
3 Foxhollow Drive Route 7, Lenox, MA
Stay at this 3-star condo in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and The Mount are located ...
The Ponds at Foxhollow
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.

Popular places to visit

St Mary's of the Assumption Church

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.

St Mary's of the Assumption Church