Windsor, MA
Travel Guide
Visit Windsor
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
$154 nightly
The price is $172 total per night from Jun 30 to Jul 1
$172 total
Jun 30 - Jul 1
Total with taxes and 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! (1,000 reviews)
"No real breakfast"
Reviewed on Jun 21, 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
$127 nightly
The price is $142 total per night from Jul 6 to Jul 7
$142 total
Jul 6 - Jul 7
Total with taxes and fees
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9.2/10 Wonderful! (1,001 reviews)
"The hot tub was welcomed after a long day of hiking the Berkshires!"
Reviewed on Jun 26, 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
$143 nightly
The price is $159 total per night from Jul 6 to Jul 7
$159 total
Jul 6 - Jul 7
Total with taxes and 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! (2,409 reviews)
"The room was great. Had everything I needed and was very comfortable."
Reviewed on Jun 24, 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! (2,409 reviews)
"The room was great. Had everything I needed and was very comfortable."
Reviewed on Jun 24, 2026
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Whitingham VT
Stay at this apartment in Whitingham. Enjoy free breakfast, a sauna, and laundry facilities. Popular attractions Harriman Reservoir and Readsboro Community Library ...
9.8/10 Exceptional! (6 reviews)
"We had a wonderful Memorial Day weekend here with our two young daughters. We enjoyed the gorgeous views, the hot tub, and the very comfortable beds. There was plenty of space for four people. Chris responded very quickly to any questions we had. A very unique home that we are happy to have made ..."
Reviewed on May 25, 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.
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- Tanglewood Music Center
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- Green Mountain National Forest
- National Shrine of the Divine Mercy
- Norman Rockwell Museum
- Williams College
- Massachusetts Museum of Contemporary Art
- Berkshire East Ski Resort
- Lee Premium Outlets
- The Mount
- Jacob's Pillow
- The Clark Art Institute
- Mount Greylock State Reservation Visitor Center
- Harriman Reservoir
- Shakespeare and Company
- Goose Pond Reservation
- Hancock Shaker Village
- Waubeeka Golf Links
- Bousquet Ski Area
- Mount Greylock
- Zoar Outdoor/Deerfield Valley Canopy Tours
- Bridge of Flowers
- Taconic Golf Club
- Berkshire Botanical Garden
- Colonial Theater
- Windsor Lake Park
- Williamstown Theatre Festival
- Deerfield River
- Berkshire Museum
- Wyndhurst Golf & Club