Cheshire
Travel Guide
Visit Cheshire
Harbour House Inn
725 North State Road Cheshire MA
The price is P15,474 per night from Dec 1 to Dec 2
P15,474
P16,356 total
Dec 1 - Dec 2
includes taxes & fees
Stay at this B&B in Cheshire. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Adams Theater and Mount Greylock State Reservation Visitor ...
9.6/10 Exceptional! (39 reviews)
Great place, great hosts, lovely experience. Would go back 100x.
Reviewed on Nov 14, 2025
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
The price is P4,364 per night from Nov 23 to Nov 24
P4,364
P5,521 total
Nov 23 - Nov 24
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 ...
8.6/10 Excellent! (2,134 reviews)
Just stayed overnight, literally there 12 hours, so was not able to take advantage of any of the amenities, but would definitely come back for a longer stay!
Reviewed on Nov 16, 2025
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
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! (755 reviews)
The suites were large. Nice to have separate bedroom. Kitchen with all the basics. Perfect for a getaway
Reviewed on Nov 14, 2025
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 ...
8.6/10 Excellent! (2,134 reviews)
Just stayed overnight, literally there 12 hours, so was not able to take advantage of any of the amenities, but would definitely come back for a longer stay!
Reviewed on Nov 16, 2025
Jiminy Peak Mountain Resort
37 Corey Rd Hancock MA
Book a stay at this ski condo in Hancock. Enjoy free parking, 2 restaurants, and 2 hot tubs. Our guests praise the property condition in our reviews. Popular ...
8.2/10 Very Good! (985 reviews)
This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the ...
Reviewed on Oct 5, 2025
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 ...
10/10 Exceptional! (7 reviews)
Healthy food too!
Reviewed on Oct 20, 2025
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.
