Cheshire
Travel Guide
Visit Cheshire
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
The price is CA $142 per night from Mar 31 to Apr 1
CA $142
CA $173 total
Mar 31 - Apr 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 ...
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
The price is CA $155 per night from Mar 4 to Mar 5
CA $155
CA $204 total
Mar 4 - Mar 5
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! (866 reviews)
Love it here. We stay a few times a year and are actually local to the hotel. Just a relaxed experience.
Reviewed on Mar 1, 2026
The Williams Inn
101 Spring Street Williamstown MA
The price is CA $266 per night from Mar 11 to Mar 12
CA $266
CA $298 total
Mar 11 - Mar 12
includes taxes & fees
Book a stay at this business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
9.6/10 Exceptional! (582 reviews)
nice aesthetics
Reviewed on Feb 24, 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 ...
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 ...
The Ponds at Foxhollow
3 Foxhollow Drive Route 7 Lenox MA
Stay at this condo in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions The Mount and Wyndhurst Golf & Club 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
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
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.
