Cheshire, MA
Travel Guide
Visit Cheshire
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
$126 nightly
The price is $141 total per night from Jan 4 to Jan 5
$141 total
Jan 4 - Jan 5, 2026
Total with taxes and 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! (2,179 reviews)
My stay was great with no problems.
Reviewed on Dec 19, 2025
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
$122 nightly
The price is $137 total per night from Jan 8 to Jan 9
$137 total
Jan 8 - Jan 9, 2026
Total with taxes and 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! (1,001 reviews)
Courteous staff
Reviewed on Dec 19, 2025
The Williams Inn
101 Spring Street Williamstown MA
$195 nightly
The price is $218 total per night from Jan 1 to Jan 2
$218 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
Book a stay at this business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
9.6/10 Exceptional! (550 reviews)
Room was very clean. Didn’t have breakfast. Staff was friendly and check in was quick.
Reviewed on Dec 7, 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
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! (2,179 reviews)
My stay was great with no problems.
Reviewed on Dec 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! (7 reviews)
Healthy food too!
Reviewed on Oct 20, 2025
The Ponds at Foxhollow
3 Foxhollow Drive Route 7 Lenox MA
Stay at this condo in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and The Mount are located ...
8.6/10 Excellent! (136 reviews)
As others have said, it’s extremely well kept and clean. In the Condo and the common areas…immaculate actually. It’s very dated. It would have been nice to know we would have people above us, and the hot tub no longer exists and that was disappointing. It’s a great location and condo is well equipped. ...
Reviewed on Dec 7, 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.
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- Jiminy Peak Mountain Resort
- Tanglewood Music Center
- National Shrine of the Divine Mercy
- Massachusetts Museum of Contemporary Art
- Green Mountain National Forest
- Williams College
- Berkshire East Ski Resort
- Bousquet Ski Area
- The Clark Art Institute
- Mount Greylock
- Norman Rockwell Museum
- Lee Premium Outlets
- The Mount
- Jacob's Pillow
- Naumkeag Museum
- Colonial Theater
- Bridge of Flowers
- Hancock Shaker Village
- Williamstown Theatre Festival
- Mount Greylock State Reservation Visitor Center
- Berkshire Botanical Garden
- Goose Pond Reservation
- Grafton Lakes State Park
- Sterling and Francine Clark Art Institute
- Berkshire Museum
- Shakespeare and Company
- Williams College Museum of Art
- Wyndhurst Golf & Club
- Zoar Outdoor/Deerfield Valley Canopy Tours
