Cheshire, MA
Travel Guide
Visit Cheshire
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
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 ...
The Black Swan Lee - Lenox, Ascend Hotel Collection
435 Laurel St, Lee, MA
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 ...
Berkshires Untold
194 Pittsfield Rd, Lenox, MA
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 ...
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
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 ...
Jiminy Peak Mountain Resort
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 ...
The Ponds at Foxhollow
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 ...
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
- Tanglewood Music Center
- Williams College
- Jiminy Peak Mountain Resort
- National Shrine of the Divine Mercy
- Green Mountain National Forest
- Massachusetts Museum of Contemporary Art
- The Clark Art Institute
- Mount Greylock
- Norman Rockwell Museum
- Jacob's Pillow
- Berkshire East Ski Resort
- The Mount
- Lee Premium Outlets
- Bousquet Ski Area
- Williamstown Theatre Festival
- Hancock Shaker Village
- Mount Greylock State Reservation Visitor Center
- Berkshire Botanical Garden
- Shakespeare and Company
- Berkshire Museum
- Naumkeag Museum
- Ventfort Hall Mansion and Gilded Age Museum
- Bridge of Flowers
- Housatonic River
- Grafton Lakes State Park
- Goose Pond Reservation
- Taconic Golf Club
- Harriman Reservoir
- Natural Bridge State Park
- Windsor Lake Park
- Colonial Theater