Windsor
Travel Guide
Visit Windsor
Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
The price is €113 per night from 27 Aug to 28 Aug
€113
27 Aug - 28 Aug
includes taxes & 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! (1,942 reviews)
"This Vacation Village is amazing, returning this week for a little time away. Stayed last week for work and came home and planned a 3 day trip based on the location."
Reviewed on 10 Aug 2025
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
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! (563 reviews)
Rest, relax, and repeat
"Great value for families! The welcoming staff, location (Lenox/Pittsfield border), spacious suite, and ample amenities made for a fantastic vacation. No free breakfast but there are several dining options and markets nearby. Gorgeous view of the sunset from the upper floors. There was a note of upcoming ..."
Reviewed on 14 Aug 2025
FairBridge Inn Express
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is €68 per night from 31 Aug to 1 Sept
€68
31 Aug - 1 Sept
includes taxes & fees
Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking ...
5.2/10 (766 reviews)
"The bathroom in our room looks like someone was murdered in the bathtub. There were stains on the bottom of the tub."
Reviewed on 10 Aug 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.
Massachusetts Vacation Rental w/ Deck & Grill
Cummington
Stay at this vacation home in Windsor. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Tannery Falls and Wahconah Falls State Park ...
9.6/10 Exceptional! (16 reviews)
Great Cabin
"Stayed with some work friends for a local outing. Great spot!"
Reviewed on 26 Jul 2025
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! (1,942 reviews)
"This Vacation Village is amazing, returning this week for a little time away. Stayed last week for work and came home and planned a 3 day trip based on the location."
Reviewed on 10 Aug 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! (962 reviews)
Good base to do things in the Berkshires
"We didn't spend much time there, but it was nice, comfortable, clean and quiet. It was close to the things we had planned to do."
Reviewed on 11 Aug 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.
