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
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is AED 474 per night from Apr 20 to Apr 21
AED 474
AED 529 total
includes taxes & fees
20 Apr - 21 Apr
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! (557 reviews)
"The hotel is cozy and charming. The rooms are well-appointed. The staff was great. Easy check-in, check-out. The bar is well stocked and they offer free (real) coffee in the morning!"

Reviewed on 14 April 2025

Life House Berkshires
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 out of 5
190 Meadow Street, South Lee, MA
Fully refundableReserve now, pay when you stay
The price is AED 393 per night from Apr 28 to Apr 29
AED 393
AED 491 total
includes taxes & fees
28 Apr - 29 Apr
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
9/10 Wonderful! (619 reviews)
"Great deal for villa resort suite. Lots of space, great condition, great amenities, great location."

Reviewed on 12 April 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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 356 per night from May 1 to May 2
AED 356
AED 398 total
includes taxes & fees
1 May - 2 May
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)
"Most everything was good. They were doing major renovation! Beds were decent, shower was nice, free breakfast buffet was great, lots to choose from! Pool was nice, but only 5 feet, but jacuzzi was wonderful! Heat was very noisy, though. Just a couple things they could have explained better in the ..."

Reviewed on 10 April 2025

The Yankee, Trademark Collection by Wyndham
See all 960 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 in-room massages. Our guests praise the helpful staff in ...
8.6/10 Excellent! (1,795 reviews)
"The location to jimney peak was great."

Reviewed on 26 March 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! (926 reviews)
"Staff was exceptionally helpful and friendly."

Reviewed on 14 January 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! (120 reviews)
"Very comfortable property in a lovely setting"

Reviewed on 18 December 2024

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