Holiday houses in New Marlborough

Gingerbread House Tower in the Berkshire Hills

Escape to this newly renovated, off-beat retreat for a magical stay. Part of Tyringham’s Gingerbread House located on the Santarella Estate in the Berkshires, Western Mass. This one-of-a-kind loft with tower bedchamber offers guests a fairytale experience. The open concept living space filled with plants brings the outdoors inside and offers ample room to relax. If looking for activity, guests can spend the day on the grounds, walking nearby trails, or exploring the many nearby Berkshire towns.

West Main

1890s home situated on the outskirts of town, entire second floor apartment. The apartment is bright and sunny and super comfortable with 2 bedrooms both with queen beds, 1 bathroom, eat in country kitchen fully equipped.There is a spacious living room with a smart Roku TV, (not cable ) WiFi and access to a private garden space, private entrance and off street parking. Walk to town brewery, pizza and more. Great place to relax after a day of exploring Litchfield county and the Berkshires.

Cosmo Cabin: Your Cozy Escape

Tucked away in the serene woods of New Marlborough, MA, Cosmo Cabin is a newly renovated 2-bed, 1-bath retreat just 3 hrs from NYC. This charming cabin offers a bright sunroom, a cozy bedroom with an electric fireplace, and a spa-like bathroom with a two-person tub for ultimate relaxation. Outside, enjoy the deck with a grill or gather around the firepit under the stars. Combining rustic charm with modern comforts, it’s the perfect escape for couples to unwind and reconnect with nature.

Grand View

Forget your worries in this spacious and serene space. Whatever your reasons for traveling you will find everything you need here. This is a great getaway but still not to far to enjoy the many amazing experiances the Berkshires has to offer. A beautiful 20 min ride to downtown Great Barrington will bring you to a variety of wonderful resturants and shopping. Or, maybe enjoy the theater, music or a movie. There is no shortage of hiking or exploring to be done. And the view is gorgous!

Cozy Tiny House • Private River & Wood Sauna

Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, an outdoor shower, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

Converted Berkshire schoolhouse on a quiet river

Renovated schoolhouse on a quiet river in the Berkshires. This is the perfect place to unwind. Great for families and friends to relax and reconnect. Take a walk to the waterfalls, play croquet on the lawn, gather dinner from our seasonal garden and enjoy 'smores around the fire pit. Very private and woodsy, but close to Butternut for skiing, Great Barrington for shopping and access to all the music and art the Berkshires has to offer. Home is stylish, comfortable and inviting.

COZY GUESTHOUSE MINUTES AWAY FROM HIKING!

Renovated 1880's one bedroom cozy guesthouse in beautiful Southfield, MA. Full kitchen stocked with all necessities. Comfortable & stylish with a luxury king size bed. Minutes away from Ski Butternut, Berkshire attractions & trails. Walking distance to breakfast and lunch at The Southfield Store or have dinner at nearby The Old Inn On The Green and Cantina 229. 10 minutes from Great Barrington. Enjoy leaf-peeping, hiking, waterfalls, apple picking, skiing, and much more!

Biggest Tiny Birdwatcher's Paradise

Welcome to Birdwatcher's Paradise! Experience acres of unspoiled wilderness as far as you can see while being surrounded by the natural songs of the Berkshires. Our home is perfect for any couple or young family looking to get away – equipped with a primary bedroom & upstairs kids loft – while only a 10min drive to GB. Enjoy a cozy seat by the wood-burning stove or a late night making s'mores & memories. Grab your binoculars and a good book, your getaway awaits!

Jaw dropping mountain & lake views

Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. Private mountain top adventure awaits.. Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.