Cheshire Travel Guide
Tourist Guide
Visit Cheshire
Harbour House Inn
725 North State Road, Cheshire, MA
The price is AU$383 per night from 9 Sept to 10 Sept
AU$383
9 Sept - 10 Sept
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 4 Jul. 2025
Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
The price is AU$202 per night from 27 Aug to 28 Aug
AU$202
27 Aug - 28 Aug
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! (1,934 reviews)
A great place to stay!
"It was a quick 1 night stay, but we would have stayed longer if we had the time! The basic suite was very large. The bed was comfortable, kitchen was well stocked with cutlery, wine glasses, etc. The front desk staff was perfectly polite and welcoming. I will say that it wasn't obvious when I booked ..."
Reviewed on 8 Aug. 2025
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
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! (547 reviews)
"Amazing place to stay. Can’t wait to go again."
Reviewed on 8 Aug. 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! (1,934 reviews)
A great place to stay!
"It was a quick 1 night stay, but we would have stayed longer if we had the time! The basic suite was very large. The bed was comfortable, kitchen was well stocked with cutlery, wine glasses, etc. The front desk staff was perfectly polite and welcoming. I will say that it wasn't obvious when I booked ..."
Reviewed on 8 Aug. 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 26 Jul. 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 ...
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.