Holiday rentals with outdoor seating in Lee

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

Berkshires Cottage by Lake. Year Round Adventures.

THE BERKSHIRES COTTAGE IN THE WOODS BY A SPRING FED LAKE HAS SOMETHING FOR EVERYONE....... SWIM, FISH, KAYAK, HIKE, SKI, JACOBS PILLOW DANCE FESTIVALS, TANGLEWOOD OUTDOOR CONCERTS, GOLF, DINE, SHOP LEE OUTLETS, DINE WITH ENTERTAINMENT, PLAYS, ANTIQUES, FIRE PITS, HANGING IN A HAMMOCK, FLOAT ON CRYSTAL CLEAR WATER, BBQ ON THE DECK, OR JUST DOING NOTHING AT ALL UNPLUG AND RECHARGE. ESCAPE & RELAX. (90 second walk through wooded path to lake) Pets Considered. $29. pet fee = approved Pet Agreement.

Enchanted Tiny Tower nestled in the Berkshires

Whimsical and romantic tower on the Santarella Estate in Tyringham, MA in the heart of the Berkshires. Live out your fairytale in this two-story unique, tiny home. First floor offers 3 rooms in one with kitchenette, sitting area, and dining room looking out on to the babbling brook. Upper bedchamber with canopied bed provides amazing views of sky and trees through massive, mill windows. Perfect destination for a relaxing getaway or special stay while exploring all the Berkshires has to offer.

Stylish Shales Brook Cottage-Cozy up to happiness

Bright & inviting! Welcome to our charming cottage, a stylish 2-bedroom, 2-bath retreat by Shales Brook. Relax on cool evenings beside the vintage Malm wood-burning stove. Enjoy modern comforts with central air, a screened-in porch, and a deck overlooking the tranquil waters of Shales Brook. The soothing sounds of the brook enhance your stay.. Located near fabulous Berkshire attractions, fantastic hikes, 15 minutes to the town of Lee, minutes to Jacob‘s pillow and 20 minutes to Tanglewood,!

Perfect Holiday Home Renovated & Fully Equipped

Welcome to Prospect Place! Our charming renovated home is set upon a hilltop overlooking downtown Lee, "The Gateway to the Berkshires." The house is in the heart of the Berkshires and central to just about everything. It is a a short drive to Tanglewood, the Berkshire Theater Festival, Jacobs Pillow and the Berkshire Outlet Mall. Golf, tennis, skiing, swimming, and spas are just minutes away. It is a perfect spot for relaxation, culture, sports, a girls weekend, and family gatherings.

Modern barn in the heart of the Berkshires

Modern, renovated dairy barn in the heart of the Berkshires. Located on 3.5 acres with beautiful views and close to everything. 1.5 miles to Main St Stockbridge/Red Lion Inn, 5 minutes to Tanglewood, 5 minutes to the Stockbridge Bowl and beautiful hiking trails, under 10 minutes to Lenox . This is the perfect base for exploring the Berkshires or a great getaway for relaxing and enjoying nature. Family and pet friendly! *Please read Interaction with Guests section before booking*

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.

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.

Boutique TINY home+private HOT TUB-walk to Main St

Blush at Art Park Homes is a romantic boutique tiny home getaway in Chatham, NY—just 2.5 hrs from NYC & Boston. Enjoy a private hot tub, firepit, dreamy loft lounge, plush queen bed, full kitchen & curated luxe design throughout. Tucked into a peaceful private oasis, yet only a 2-min walk to Main St. restaurants, brewery, shops & theater. Perfect for couples seeking a unique Hudson Valley getaway near hiking, galleries & great dining. @artparkhomes

HOT TUB! Dog & Family Friendly in the Berkshires!

Secluded Berkshires Retreat! -Dog/s, Family Friendly cottage -Freshly painted & new floors for 2026! -Patio w/ Hot tub, fire pit, canoe use -Acre secluded lot -Historic Lee, Stockbridge, Lenox/Tanglewood, Norman Rockwell Museum w/in 30 min! -30 min Monument Mt. & Berkshires Scenic Railway -Appalachian Trail hiking -Wineries/Breweries -Outlets/Small Shops -Master w/Queen -2nd bed with 1 Twin/Full Bunk -Full size pull out couch

Artist Cottage

Artsy vintage cottage with a private lodge in a quiet Berkshire neighborhood. Backyard opens to woods with trails nearby. Enjoy fireplaces and hot tub in winter, waterfall and outdoor shower in summer. Upstairs queen ensuite with bathroom and soaking tub; downstairs retro kitchen, living room, and full bath with shower. Lodge offers comfy seating, farm table, and big-screen TV. High-speed internet, Prime & Spectrum TV.

Comfy cabin with scenic views in the Berkshires

The Beaver Dam is a sunlight-filled & recently renovated cabin tucked in the woods, overlooking the October Mountain State Park and steps away from Basin Pond. We are located close to a number of excellent ski slopes. Our cottage is the last house on a private road and right next to protected forest. You can't ask for more privacy, peace and quiet than you'll find at our little piece of paradise on the pond!