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Fall Foliage Luxury Cabin & View Autumn Adventures

Welcome to our mountain retreat, nestled in the heart of nature and brought to you by Den Outdoors. 25 mins to Tanglewood, 35 mins to Jacobs Pillow, 15 mins to Jiminy Peak, 30 mins to The Clark, MASS MoCA, and the Berkshire region. 10 mins to a swimmable lake. 2.5 hrs from NYC and from Boston. Come experience all Autumn has to offer! Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit, large Webber Grill, radiant floor, EV charging, and the MOST STUNNING view!

Berkshire 4 season home

The house is located in the heart of the Berkshires. It's less than 10 miles from Tanglewood, Kripalu, Jacob's pillow Dance, Monument Mountain, Beartown state forest, Norman Rockwell Museum, Shakespeare & Co., Ski Butternut, Lee Prime outlets. Located 1.5 miles from the turnpike exit for easy travel, 3 miles from Laurel lake, walking distance to a public golf course and downtown Lee where you will find great restaurants. There is Cable internet that is fast and reliable if you have to work.

Home away from home: Minutes to Tanglewood.

Welcome to your home away from home! This charming 3-bedroom, 2.5-bathroom stylishly decorated home blends comfort and style in the Berkshires. It features a bedroom with a king, a bedroom with a queen, and one bedroom with a king and a twin over double bunk bed. Lots of couches and seating also. The kitchen has been refreshed with a table for 10. In the basement is a media room for movies and quiet time. We welcome you to our home and hope you enjoy your stay. Close to Tanglewood.

Modern Chalet Near Tanglewood & Downtown Lenox

Your Modern Berkshires Escape Light-filled modern chalet next to Kennedy Park with beautiful views, a spacious living room, and a peaceful garden for morning coffee, evening wine or yoga. Designed for families and friends, with a private upstairs main suite plus comfortable guest rooms. Minutes to Tanglewood, downtown Lenox, hiking trails, lakes, great dining, and the best of the Berkshires. Perfect for a summer getaway filled with music, nature, and time to unwind. Healthy fun!

Cozy cottage on peaceful pond

This little slice of heaven is located on the serene Richmond Pond. Right down the street from Balderdash winery and a 15 minute drive to charming downtown Lenox and Tanglewood. In Lenox you can find great dining, shopping, and there is plenty of hiking and biking around this area. This cozy cottage has everything you need for a Berkshire retreat. In the fall cozy up next to the fireplace inside or out take a break and unwind at this Peaceful oasis. 

Lovely Downtown Lenox apt, walk to everything!

Experience the best of the Berkshires in a beautiful, spacious apartment right in the center Lenox. This updated space is filled with natural light and hardwood floors, great for families or friends looking to experience culture and countryside. Walking distance to Tanglewood, Shakespeare & Co, Kennedy Park, restaurants, and shopping. On second floor of a Historic building with a deck that has a birds eye view of town. 7 min to Bousquet Mountain.

Historical Downtown 1 Bedroom Apartment

Located in the heart of historical downtown Lenox. A beautifully renovated space fully equipped for all your needs. The eat-in kitchen has a table for two, stainless appliances, and an array of cooking essentials. The living room features a comfortable sectional and a flat screen TV for relaxing. Wi-Fi is available throughout the space. Central heat and air to provide a comfortable environment in any season. All linens and towels are provided.

The Penthouse, Downtown Lenox by Evergreen Home

Evergreen Home Vacation Rentals invites you to experience luxury in the heart of Lenox. Just 10 minutes from Bousquet Mountain, this beautifully renovated 3-bedroom, 2-bath downtown apartment blends elevated design with modern comfort. Every detail has been thoughtfully curated—from plush Parachute and Annie Selke linens to radiant heated bathroom floors. Enjoy dinner downtown, then retreat to complete serenity just steps away. ✨

Historic Haven at 93 Church St.

Welcome to your charming retreat on Church Street — a spacious, thoughtfully appointed 2-bedroom, 1.5-bath home nestled in the heart of idyllic downtown Lenox. This beautifully preserved historic property combines timeless character with modern comfort, featuring exposed wood beams, tasteful decor, and all the essentials for a relaxing stay.

GreenHouse

Relax and enjoy the Berkshires at this peaceful place to stay in the beautiful Berkshires of western Massachusetts. GreenHouse is the guest cottage for the historic Hyde House which is on the National Register of Historic Places. Located within walking distance of Lee, Ma, the house is also conveniently located near Stockbridge and Lenox.

The Berkshire Quintessential Cape downtown Lenox

Experience the Best of the Berkshires in the Heart of Lenox Welcome to this charming, in-town Lenox retreat—where classic Berkshire character meets thoughtful design. Bathed in natural light, the home features stunning oak floors, crisp white walls and an abundance of windows that create a bright, airy atmosphere throughout.

Spacious 3 bedroom apt in Lenox historic downtown

Newly renovated, spacious 3-bedroom apartment, with 2 bathrooms and free parking in the back. Centrally located in the heart of historic downtown of Lenox. Walk to restaurants and shops, or even skip the traffic and take the 15 min walk to Tanglewood, the famous summer home of Boston Symphony Orchestra .