Holiday houses in Stockbridge Bowl

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Cozy, welcoming Berkshires cabin – come unplug!

Charming, comfortable cottage tucked away in a serene setting in Mahkeenac Heights. Step back to a time when things were simpler, less hurried. Prime location between Stockbridge and Lenox centers, 7 minutes to Tanglewood, short walk or 2 minute drive to Stockbridge Town Beach. The cottage features an open living and dining room with fieldstone fireplace, galley kitchen, glass enclosed 3 season porch, 2 bedrooms, and a sleeping loft with 2 single beds. Back yard with deck, hammock and fire pit.

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.

Kayak on Prospect Lake, Paddle Boards, Swim Dock+!

Due to last minute Cancelation, August 2026 dates available - please inquire! Amenities: 3 bedroom, 1 bath, sleeps 5 or 7 max. waterfront direct on Prospect Lake with dock and swim ladder, sun deck, bar and seating, propane BBQ grill, 2 kayaks, 2 canoes, 2 paddle board, floats. fishing rods, outdoor dining, exterior lighting, fire pit, central AC, washer/dryer, dishwasher, gas fireplace, and more! Quiet, well trained dogs welcome with a $150 pet fee, per pet. Strict on-leash laws apply.

Hip Stockbridge Cabin - A stroll to the lake

Welcome to our stylish glamping cabin! Relax in the spacious yard & sunny deck. Cozy fieldstone fireplace, vaulted ceilings & skylights. The cottage features gorgeous pine wood & fantastic interior design. Unwind in the reading nook, master bedroom with skylights, or put on your favorite vinyl. Kids will adore the sleeping loft. Just a 9-minute walk or 2-minute drive to the public beach (the beautiful Stockbridge Bowl). BBQ grill, outdoor fire pit . Tanglewood is just minutes away.

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

Lakeshore cabin with beach and dock

A classic Berkshire cabin nestled under maple trees, on the shore of the Stockbridge Bowl cove. Serene, peaceful and private, yet close to all area attractions. Large light-filled living room with cathedral ceiling and skylights. Main bedroom on ground floor with bathroom. Enclosed porch and large deck with gas grill. Swimming and kayaking off the dock. Large lawn with lots of trees. Forest trail and waterfall next door. Plenty of parking. 5 minutes to Tanglewood and Kripalu.

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.

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. 

Modern studio with views of the treetops

Our Stockbridge studio is located at the heart of the Berkshires, just north of the center of town. It is a new, modern, second floor studio suitable for up to four adults with views of the surrounding woods, a large kitchenette and comfortable, spacious living space for relaxing in your home away from home. There is a full bath and a private entrance. It is perfect for a weekend getaway or a seasonal stay, whatever your heart desires.

Stockbridge Landings | 3 Mins To Tanglewood

Welcome to our rustic summer cottage—quaint, quirky, and perfectly imperfect! Nestled right at the Stockbridge Bowl in the Berkshires, it’s the spot for water lovers and Tanglewood fans alike. With more charm than shiny new, this cozy retreat is ideal for those who appreciate rustic charm and a splash of personality. Just 3 minutes from Tanglewood, it’s a step back in time where moments with family abound and good times float freely!

Summer Mountain Retreat + Views, Fire Pit, Hot Tub

Escape to your modern mountain retreat—perfect for Summer getaways! Just 15 mins to Tanglewood, MASS MoCA & The Clark, and close to scenic hikes, waterfalls, farm stands, breweries, and charming small towns. Soak in the wood-fired hot tub, enjoy evenings around the Breeo fire pit, cook fresh seasonal meals, and unwind in peaceful privacy. With EV charging and a quiet workspace, it’s ideal for refreshing escapes or Summer adventures.