Cheshire
Travel Guide
Visit Cheshire
Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
The price is P5,308 per night from Nov 2 to Nov 3
P5,308
P6,564 total
Nov 2 - Nov 3
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! (2,020 reviews)
"Absolutely fantastic!!! This just be our new escape from reality place. Everything was top shelf."
Reviewed on Sep 28, 2025
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
The price is P5,394 per night from Nov 2 to Nov 3
P5,394
P7,318 total
Nov 2 - Nov 3
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! (662 reviews)
"Very convenient set up of both room and kitchen, resort very easy to navigate."
Reviewed on Sep 28, 2025
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
The price is P6,719 per night from Nov 2 to Nov 3
P6,719
P8,313 total
Nov 2 - Nov 3
includes taxes & fees
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
9/10 Wonderful! (745 reviews)
"Lovely unit with everything you need for one night or a month. Great activity space with plenty to do."
Reviewed on Oct 4, 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! (2,020 reviews)
"Absolutely fantastic!!! This just be our new escape from reality place. Everything was top shelf."
Reviewed on Sep 28, 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! (979 reviews)
"Cool"
Reviewed on Sep 19, 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! (4 reviews)
"Great Time! Beautiful new tents with all the items you need to Glamp with from silverware to tupperware. Comfy beds and comforter! Everyone was so nice and you know they love what they do! Next fall/foiliage camping in the trapper with the wood stove !"
Reviewed on Aug 25, 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.
