Cheshire, MA
Travel Guide
Visit Cheshire
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
The price is NT$5,113 per night from Jun 15 to Jun 16
NT$5,113
NT$5,711 total
Jun 15 - Jun 16
includes taxes & fees
Book a stay at this business-friendly hotel in North Adams. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,009 reviews)
"Clean simple, functional, nice all day coffee tea station"
Reviewed on 2026/6/8
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundable
The price is NT$4,446 per night from Jul 12 to Jul 13
NT$4,446
NT$5,674 total
Jul 12 - Jul 13
includes taxes & fees
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (974 reviews)
"Staff, breakfast, spaciousness of the room, all fabulous."
Reviewed on 2026/6/11
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
The price is NT$3,531 per night from Jun 24 to Jun 25
NT$3,531
NT$4,291 total
Jun 24 - Jun 25
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 ...
8.8/10 Excellent! (2,392 reviews)
"This is a big beautful modern condo complex about 20 mins outside Wiilamstown (to the north) or Pittsfield (to the south). Huge swimming pools - one indoors, one out. Beautiful views of the Berkshires. Quiet rural environment. I could hear the frogs singing and the cricketa chirp at night. Excellent ..."
Reviewed on 2026/6/8
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 ...
8.8/10 Excellent! (2,392 reviews)
"This is a big beautful modern condo complex about 20 mins outside Wiilamstown (to the north) or Pittsfield (to the south). Huge swimming pools - one indoors, one out. Beautiful views of the Berkshires. Quiet rural environment. I could hear the frogs singing and the cricketa chirp at night. Excellent ..."
Reviewed on 2026/6/8
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 ...
9.4/10 Exceptional! (10 reviews)
"Excelente servicio"
Reviewed on 2026/3/8
The Ponds at Foxhollow
3 Foxhollow Drive Route 7 Lenox MA
Stay at this aparthotel 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! (141 reviews)
"I had not visited the Ponds for 30 years. It has not gracefully aged. Condo unit has not been updated since it was built in the early 70s and it shows. Drafty and slightly damaged doors, slow drains in the bathrooms, furniture and rugs that show damage and age, and a clubhouse in need of updating. ..."
Reviewed on 2026/2/9
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
5/5(1 review)
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.
- Norman Rockwell Museum
- Massachusetts Museum of Contemporary Art
- National Shrine of the Divine Mercy
- The Clark Art Institute
- Mount Greylock State Reservation Visitor Center
- Lee Premium Outlets
- Goose Pond Reservation
- Colonial Theater
- Grafton Lakes State Park
- Bridge of Flowers
- Windsor Lake Park
- Berkshire Botanical Garden
