Cheshire, MA
Travel Guide
Visit Cheshire
Harbour House Inn
725 North State Road, Cheshire, MA
The price is NT$8,079 per night from Oct 29 to Oct 30
NT$8,079
NT$8,539 total
Oct 29 - Oct 30
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 2025/9/12
Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
The price is NT$2,825 per night from Nov 12 to Nov 13
NT$2,825
NT$3,494 total
Nov 12 - Nov 13
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! (2,097 reviews)
Check in was easy. Room was clean and well-stocked. Lay out for the double room was great. Pool was well-maintained. Game room was added benefit. Very nice stay.
Reviewed on 2025/10/24
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
The price is NT$2,364 per night from Nov 26 to Nov 27
NT$2,364
NT$3,329 total
Nov 26 - Nov 27
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! (723 reviews)
We loved this place. Quiet, very clean,attractive. Loved that it had a kitchen area. Second story, sliding glass doors overlooked the fall foliage in the back of the building. Very peaceful..
Reviewed on 2025/10/22
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! (2,097 reviews)
Check in was easy. Room was clean and well-stocked. Lay out for the double room was great. Pool was well-maintained. Game room was added benefit. Very nice stay.
Reviewed on 2025/10/24
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! (984 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 2025/10/5
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 2025/10/20
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.
- National Shrine of the Divine Mercy
- Massachusetts Museum of Contemporary Art
- The Clark Art Institute
- Norman Rockwell Museum
- Lee Premium Outlets
- Bousquet Ski Area
- Mount Greylock State Reservation Visitor Center
- Berkshire Botanical Garden
- Williamstown Theatre Festival
- Grafton Lakes State Park
- Bridge of Flowers
- Goose Pond Reservation
