Cheshire, MA
Travel Guide
Visit Cheshire
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
The price is ￥18,491 per night from May 31 to Jun 1
￥18,491
￥24,213 total
May 31 - Jun 1
includes taxes & fees
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (953 reviews)
"It's so comfortable"
Reviewed on May 26, 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
The price is ￥17,085 per night from Jun 10 to Jun 11
￥17,085
￥19,084 total
Jun 10 - Jun 11
includes taxes & fees
Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
9/10 Wonderful! (961 reviews)
"Friendly good location"
Reviewed on May 26, 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
The price is ￥19,154 per night from May 31 to Jun 1
￥19,154
￥23,142 total
May 31 - Jun 1
includes taxes & fees
Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,373 reviews)
"Clean room great check in process smooth easy going. Jacuzzi was great, very cleaned!"
Reviewed on May 27, 2026
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
Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,373 reviews)
"Clean room great check in process smooth easy going. Jacuzzi was great, very cleaned!"
Reviewed on May 27, 2026
The Ponds at Foxhollow
3 Foxhollow Drive Route 7 Lenox MA
Stay at this aparthotel 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! (141 reviews)
"I had not visited the Ponds for 30 years. It has not gracefully aged. Condo unit has not been updated since it was built in the early 70s and it shows. Drafty and slightly damaged doors, slow drains in the bathrooms, furniture and rugs that show damage and age, and a clubhouse in need of updating. ..."
Reviewed on Feb 9, 2026
Huttopia Berkshires
312 Kittle Rd Williamstown MA
Stay at this campground in Williamstown. Enjoy free parking, breakfast (surcharge), and a picnic area. Popular attractions Jiminy Peak Mountain Resort and Mountain ...
9.4/10 Exceptional! (10 reviews)
"Excelente servicio"
Reviewed on Mar 8, 2026
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)
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.
