Cheshire, MA
Travel Guide
Visit Cheshire
Harbour House Inn
725 North State Road, Cheshire, MA
The price is ₩364,274 per night from Aug 13 to Aug 14
₩364,274
₩385,037 total
Aug 13 - Aug 14
includes taxes & fees
Stay at this 3.5-star B&B in Cheshire. Enjoy free breakfast, free WiFi, and free parking. Popular attractions St Mary's of the Assumption Church and Adams Theater ...
9.6/10 Exceptional! (37 reviews)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!!"
Reviewed on Jul 4, 2025
Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
The price is ₩150,430 per night from Aug 27 to Aug 28
₩150,430
₩183,265 total
Aug 27 - Aug 28
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! (1,938 reviews)
"This Vacation Village is amazing, returning this week for a little time away. Stayed last week for work and came home and planned a 3 day trip based on the location."
Reviewed on Aug 10, 2025
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
The price is ₩106,595 per night from Sep 7 to Sep 8
₩106,595
₩150,091 total
Sep 7 - Sep 8
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! (554 reviews)
"It was a great stay. The couches in the room were dirty and should be replaced."
Reviewed on Aug 11, 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! (1,938 reviews)
"This Vacation Village is amazing, returning this week for a little time away. Stayed last week for work and came home and planned a 3 day trip based on the location."
Reviewed on Aug 10, 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! (959 reviews)
"Great"
Reviewed on Jul 26, 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! (2 reviews)
"Perfect place for a relaxing getaway! We loved everything!"
Reviewed on Aug 11, 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
Learn about the local history of Cheshire with a stop at St Mary's of the Assumption Church. Discover the area's mountain views, or seek out its ski slopes.