Cheshire, MA
Travel Guide
Visit Cheshire
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
The price is AED 434 per night from Apr 5 to Apr 6
AED 434
AED 485 total
5 Apr - 6 Apr
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 ...
8.8/10 Excellent! (1,000 reviews)
For the price, is a good property. Convenient for our purposes. While not up to more modern standards, it is reasonably furnished. Location is a bit noisy due to traffic and trains. Limited decent food options.
Reviewed on 5 March 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
The price is AED 334 per night from Mar 22 to Mar 23
AED 334
AED 456 total
22 Mar - 23 Mar
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! (878 reviews)
The room is cozy and the kitchen is great. The pool area needs renovation but my kids still love the fact the pool is huge. Only downside is it takes forever to get your $150 deposit refunded:( every time and I leave the room spotless.
Reviewed on 17 March 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
The price is AED 257 per night from Apr 1 to Apr 2
AED 257
AED 287 total
1 Apr - 2 Apr
includes taxes & fees
Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
9/10 Wonderful! (876 reviews)
I always sleep the best here. So quiet and comfortable. Love the lounge area. Bartender really nice. Had a lovely cheese plate. Shower is great. Great value!
Reviewed on 18 March 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.
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 8 March 2026
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! (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 9 February 2026
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 ...
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.
