Cheshire, MA
Travel Guide
Visit Cheshire

Harbour House Inn
725 North State Road, Cheshire, MA
$236 nightly
The price is $250 total per night from Sep 10 to Sep 11
$250 total
Sep 10 - Sep 11
Total with taxes and 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
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $145 total per night from Aug 27 to Aug 28
$145 total
Aug 27 - Aug 28
Total with taxes and 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! (1,957 reviews)
"A rare, affordable place in the Berkshires! The scenery is stunning, and we loved the pools (both indoor and out) and fire pit. The staff was friendly, and our room was spacious but dated: the blinds were broken, the doors stuck, the walls were paper thin and our king-size mattress had clearly seen ..."
Reviewed on Aug 18, 2025

Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
$108 nightly
The price is $120 total per night from Sep 7 to Sep 8
$120 total
Sep 7 - Sep 8
Total with taxes and 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! (586 reviews)
"I stayed here for a work trip to a remote project site. This place was very impressive for the money. The rooms were large and had everything. The place was clean and staff very pleasant and accommodating. I didn’t expect a lot for what I paid but was pleasantly surprised."
Reviewed on Aug 23, 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! (1,957 reviews)
"A rare, affordable place in the Berkshires! The scenery is stunning, and we loved the pools (both indoor and out) and fire pit. The staff was friendly, and our room was spacious but dated: the blinds were broken, the doors stuck, the walls were paper thin and our king-size mattress had clearly seen ..."
Reviewed on Aug 18, 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! (966 reviews)
Beautiful Berkshire relaxation!
"From the pleasant staff to the comfy cozy, clean atmosphere of the room, this resort is a definite “go to” experience while vacationing in the Berkshires. The resort attractions are a family fun filled adventures that are great to experience. Our favorite was the ski lift to the top of the mountain ..."
Reviewed on Aug 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! (3 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.
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- Tanglewood Music Center
- Jiminy Peak Mountain Resort
- Williams College
- Green Mountain National Forest
- National Shrine of the Divine Mercy
- Massachusetts Museum of Contemporary Art
- Mount Greylock
- Berkshire East Ski Resort
- The Clark Art Institute
- Norman Rockwell Museum
- Lee Premium Outlets
- Jacob's Pillow
- The Mount
- Bousquet Ski Area
- Mount Greylock State Reservation Visitor Center
- Naumkeag Museum
- Hancock Shaker Village
- Ventfort Hall Mansion and Gilded Age Museum
- Berkshire Botanical Garden
- Zoar Outdoor/Deerfield Valley Canopy Tours
- Berkshire Museum
- Taconic Golf Club
- Williamstown Theatre Festival
- Grafton Lakes State Park
- Harriman Reservoir
- Shakespeare and Company
- Bridge of Flowers
- Berkshire Mountain Country Store
- Goose Pond Reservation
- Natural Bridge State Park