Windsor, MA
Travel Guide
Visit Windsor
![Hotel Downstreet](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/644e76fa_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Hotel Downstreet
40 Main St, North Adams, MA
The price is $149 per night from Jun 23 to Jun 24
$149
$166 total
includes taxes & fees
Jun 23 - Jun 24
Stay at this hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our ...
8.4/10 Very Good! (931 reviews)
Nifty hotel in a great little town
"The room was clean and distinctive. Everything worked properly. The hotel is perfectly located for accessing anything in town by foot, including MassMOCA and various eateries."
Reviewed on Jun 16, 2024
![Life House Berkshires](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/967b0257_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Life House Berkshires
194 Pittsfield Rd, Lenox, MA
The price is $119 per night from Jun 24 to Jun 25
$119
$133 total
includes taxes & fees
Jun 24 - Jun 25
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (267 reviews)
Great place
"High end feel at a budget friendly price. The room was boho fun but needs a few tweaks. I still give it 5 stars but wish that they had a variety of pillows on the bed, they were very nice but too thick for a stomach or back sleeper. There is a full mini bar with prices only available by QR reader, ..."
Reviewed on Jun 19, 2024
![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/96ff6d07_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
The price is $125 per night from Jun 26 to Jun 27
$125
$140 total
includes taxes & fees
Jun 26 - Jun 27
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 ...
9/10 Wonderful! (1,001 reviews)
Pleasantly surprised
"We had a good experience here! The staff was AWESOME! They were very helpful in checking in and gave us good info. They have a bar but it was not open during the times we were in and out. The breakfast was good and we enjoyed the omelet. Its only on the weekend--wish it was every day! The pool was ..."
Reviewed on Jun 15, 2024
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.
![Jiminy Peak Mountain Resort](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/eea5dbe7_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
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 bars/lounges. Our guests praise the helpful staff and the clean rooms in our ...
8/10 Very Good! (858 reviews)
"This is a sweet property. I visited in the summer. The dining options were great. The country store is awesome. I love how the rooms are suites. They feel like small apartments. I like that they have kitchens. The bed was comfortable. The ac is loud but at least it works well and it drowns out other ..."
Reviewed on Jun 17, 2024
![Pristine Home In Becket Woods](https://images.trvl-media.com/lodging/84000000/83270000/83269800/83269705/79263c62_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Pristine Home In Becket Woods
Becket
Stay at this vacation home in Becket. Enjoy patios, Netflix, and in-room jetted tubs. Popular attractions Becket Land Trust Historic Quarry and Chester Town ...
10/10 Exceptional! (8 reviews)
Beautiful Home and Location
"I really loved my stay at this beautiful property surrounded by nature and peacefulness in the Berkshire mountains. The owners were great too with communication and making things easy for check in and check out. Highly recommend this place!"
Reviewed on May 29, 2024
![Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating](https://images.trvl-media.com/lodging/20000000/19220000/19210700/19210630/20b0b507_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Becket
Stay at this cabin in Becket. Enjoy a garden, patios, and cable/satellite TV service. Our guests praise the clean rooms in our reviews. Popular attractions Pyramid ...
9.4/10 Exceptional! (165 reviews)
Sherwood Forest Gem
"We’ve stayed at the cabin with our dog four times and always enjoy our peaceful stay. It’s cozy, clean and private. Also, the Sherwood Shoppe - just down the road - is a wonderful place for breakfast, homemade chili and much more."
Reviewed on May 1, 2024
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.
- Tanglewood Music Center
- Jiminy Peak Mountain Resort
- Williams College
- National Shrine of the Divine Mercy
- Massachusetts Museum of Contemporary Art
- Norman Rockwell Museum
- Lee Premium Outlets
- Mount Greylock
- The Clark Art Institute
- Jacob's Pillow
- The Mount
- Berkshire East Ski Resort
- Bousquet Ski Area
- Hancock Shaker Village
- Shakespeare and Company
- Mohawk Trail State Forest
- October Mountain State Forest
- Mount Greylock State Reservation Visitor Center
- Ventfort Hall Mansion and Gilded Age Museum
- Pittsfield State Forest
- Savoy Mountain State Forest
- Wyndhurst Golf & Club
- Naumkeag Museum
- Barrington Stage Company
- Berkshire Museum
- Bridge of Flowers
- Colonial Theater
- Williamstown Theatre Festival
- Berkshire Botanical Garden
- Berkshire Mountain Country Store
- Zoar Outdoor/Deerfield Valley Canopy Tours
- Goose Pond Reservation