Cheshire
Travel Guide
Visit Cheshire
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is P5,299 per night from May 24 to May 25
P5,299
P7,269 total
May 24 - May 25
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! (925 reviews)
Room very spacious and clean. Full kitchen is a great bonus.
Reviewed on May 4, 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
The price is P6,067 per night from May 26 to May 27
P6,067
P6,777 total
May 26 - May 27
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! (932 reviews)
Easy, comfortable and convenient; rooms and public spaces are nice, modern and stylish updates of modest 60s/70s original motel facilities.
Reviewed on May 6, 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
The price is P5,211 per night from May 12 to May 13
P5,211
P6,483 total
May 12 - May 13
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! (2,351 reviews)
I loved my stay at the resort! The view was beautiful, my room was clean, and the staff were nice. I had trouble with my door, and they sent someone quickly to fix it.
Reviewed on May 8, 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 ...
8.8/10 Excellent! (2,351 reviews)
I loved my stay at the resort! The view was beautiful, my room was clean, and the staff were nice. I had trouble with my door, and they sent someone quickly to fix it.
Reviewed on May 8, 2026
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 National Shrine of the ...
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 Feb 9, 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 ...
9.4/10 Exceptional! (10 reviews)
Excelente servicio
Reviewed on Mar 8, 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.
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.
