Cheshire
Travel Guide
Visit Cheshire
Harbour House Inn
725 North State Road, Cheshire, MA
The price is RM1,109 per night from 27 Oct to 28 Oct
RM1,109
RM1,173 total
27 Oct - 28 Oct
includes taxes & fees
Stay at this 3.5-star B&B in Cheshire. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Adams Theater and Mount Greylock State Reservation ...
9.6/10 Exceptional! (38 reviews)
The owner Brandi was outstanding, friendly, she made us fresh homemade breakfast each morning, which the best. Will differently stay there again. Wonderful place and people.
Reviewed on 12 Sept 2025
Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
The price is RM388 per night from 2 Nov to 3 Nov
RM388
RM480 total
2 Nov - 3 Nov
includes taxes & fees
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 ...
8.6/10 Excellent! (2,078 reviews)
The place is immaculate . Everyone at front desk very helpful . The grounds are beautifully landscaped . Has all the amenities of home . My hubby joked and said he'd move into this room for his retirement . Lots of nice restaurants in the area . Shops and beauty all around .
Reviewed on 18 Oct 2025
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
The price is RM394 per night from 2 Nov to 3 Nov
RM394
RM535 total
2 Nov - 3 Nov
includes taxes & fees
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (716 reviews)
Yes, everything was very well set up. Thanks.
Reviewed on 19 Oct 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
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 ...
8.6/10 Excellent! (2,078 reviews)
The place is immaculate . Everyone at front desk very helpful . The grounds are beautifully landscaped . Has all the amenities of home . My hubby joked and said he'd move into this room for his retirement . Lots of nice restaurants in the area . Shops and beauty all around .
Reviewed on 18 Oct 2025
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 hot tubs. Our guests praise the property condition in our reviews. Popular ...
8.2/10 Very Good! (982 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 5 Oct 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 20 Oct 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.
