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
The price is AED 431 per night from Jun 17 to Jun 18
AED 431
AED 481 total
17 Jun - 18 Jun
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! (1,002 reviews)
"Lovely staff!"

Reviewed on 31 May 2025

The Yankee, Trademark Collection by Wyndham
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Black Swan Lee - Lenox, Ascend Hotel Collection
3 out of 5
435 Laurel St, Lee, MA
The price is AED 468 per night from Jun 12 to Jun 13
AED 468
AED 523 total
12 Jun - 13 Jun
includes taxes & fees
Stay at this 3-star hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular ...
9/10 Wonderful! (1,002 reviews)
Oh oh New England!
"The Black Swan is a reliable stay. If you are passing through, get the cheaper rooms on the parking lot side, if you are staying for a few nights get a room with a lake view and balcony. Not a chain!"

Reviewed on 4 June 2025

The Black Swan Lee - Lenox, Ascend Hotel Collection
Berkshires Untold
Berkshires Untold
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is AED 955 per night from Jun 7 to Jun 8
AED 955
AED 1,067 total
7 Jun - 8 Jun
includes taxes & fees
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (600 reviews)
"Great spot for hitting hiking spots"

Reviewed on 27 May 2025

Berkshires Untold
See all 984 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! (1,815 reviews)
"Children on the floor above ran around and it was very loud for about three hours while we were trying to go to sleep. The rooms were as advertised. Staff was friendly and helpful."

Reviewed on 1 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! (931 reviews)
"Beautiful scenery"

Reviewed on 28 May 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