Cheshire
Travel Guide
Visit Cheshire
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
The price is P6,120 per night from Jan 6 to Jan 7
P6,120
P7,482 total
Jan 6 - Jan 7
includes taxes & fees
Book a stay at this 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! (2,197 reviews)
The rooms are clean, the pool is nice and the location is perfect for Jiminy Peak!
Reviewed on Jan 2, 2026
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
The price is P6,827 per night from Feb 2 to Feb 3
P6,827
P7,626 total
Feb 2 - Feb 3
includes taxes & fees
Book a stay at this business-friendly hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,002 reviews)
friendly accommodating staff
Reviewed on Jan 1, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
The price is P5,768 per night from Jan 9 to Jan 10
P5,768
P6,443 total
Jan 9 - Jan 10
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (1,004 reviews)
Staff was very pleasant and friendly. From front desk to valet.
Reviewed on Jan 1, 2026
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
Book a stay at this 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! (2,197 reviews)
The rooms are clean, the pool is nice and the location is perfect for Jiminy Peak!
Reviewed on Jan 2, 2026
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 Oct 20, 2025
Jiminy Peak Mountain Resort
37 Corey Rd Hancock MA
Book a stay at this 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! (988 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 Oct 5, 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.
