Windsor, MA
Travel Guide
Visit Windsor
Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
$130 nightly
The price is $145 total per night from Aug 27 to Aug 28
$145 total
Aug 27 - Aug 28
Total includes 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! (1,938 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 Aug 10, 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 includes 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! (554 reviews)
"It was a great stay. The couches in the room were dirty and should be replaced."
Reviewed on Aug 11, 2025
FairBridge Inn Express
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $84 total per night from Aug 12 to Aug 13
$84 total
Aug 12 - Aug 13
Total includes taxes and 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 (764 reviews)
"This family is professional and kind. I left a $100 tip because I watched attend to her guests and her two Autistic sons as well as her elderly parent. Amazing"
Reviewed on Aug 2, 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 Jul 26, 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! (1,938 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 Aug 10, 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! (959 reviews)
"Great"
Reviewed on Jul 26, 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.
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- Tannery Falls
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- 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
- Harriman Reservoir
- Shakespeare and Company
- Bridge of Flowers
- Berkshire Mountain Country Store
- Goose Pond Reservation
- Natural Bridge State Park
- Colonial Theater
- Deerfield River