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
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is SAR 447 per night from Jun 30 to Jul 1
SAR 447
SAR 499 total
30 Jun - 1 Jul
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 ...
9/10 Wonderful! (1,000 reviews)
"Quiet, clean, great proximity to places and destinations."

Reviewed on 18 June 2025

The Yankee, Trademark Collection by Wyndham
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
The price is SAR 380 per night from Jul 1 to Jul 2
SAR 380
SAR 424 total
1 Jul - 2 Jul
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,000 reviews)
"good stay, clean friendly and it was nice to be able to open the window in the room for fresh clean air. only drawback was it is close to the road and road noise was a little annoying. our room was facing the road and we had the window open so it was a trade off"

Reviewed on 14 June 2025

Best Western Plus Berkshire Hills Inn & Suites
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
The price is SAR 390 per night from Jun 24 to Jun 25
SAR 390
SAR 477 total
24 Jun - 25 Jun
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! (1,828 reviews)

Reviewed on 16 June 2025

Vacation Village in the Berkshires
See all 989 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! (1,828 reviews)

Reviewed on 16 June 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 bars/lounges. Our guests praise the property condition in our reviews. Popular ...
8.2/10 Very Good! (933 reviews)
"Summer stay not during ski season. Staff very helpful, welcoming, friendly. Room was clean and nice although some people might consider the main lodging building where I stayed would be outdated. But it was a very good experience all around. Beautiful natural surroundings all around the area so it’s ..."

Reviewed on 9 June 2025

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 ...
8.6/10 Excellent! (121 reviews)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."

Reviewed on 14 May 2025

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

5/5(1 review)

Learn about the local history of Cheshire with a stop at St Mary's of the Assumption Church. Discover the area's mountain views, or seek out its ski slopes.

St Mary's of the Assumption Church