Holiday houses in New Marlborough

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Top-rated holiday rentals in New Marlborough

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Guest favourite

Chalet in Otis

4.95 out of 5 average rating, 419 reviews

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

Top Guest favourite

Home in New Marlborough

5 out of 5 average rating, 9 reviews

Cottage in the heart of Mill River Village

River Cottage /Mill River hugs the Konkapot river with idyllic small town flavor.....This village boasts a General Store and a library steps away from River Cottage. Walk to Umpachene Falls for a swim or take one of 6 hikes here in town. River Cottage has an ensuite on the first floor, a country kitchen and first floor laundry. A second floor family room is equipped for family movies or streaming. Open the windows in any room and hear the river passing by... Enjoy outdoor gardens and patio.

Top Guest favourite

Treehouse in Tyringham

4.99 out of 5 average rating, 298 reviews

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.

Top Guest favourite

Apartment in Canaan

4.99 out of 5 average rating, 144 reviews

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.

Superhost

Cabin in New Marlborough

5 out of 5 average rating, 3 reviews

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.

Top Guest favourite

Apartment in Sheffield

5 out of 5 average rating, 367 reviews

Hideaway with Spectacular Berkshire Views

Located on the border of Massachusetts and Connecticut with spectacular views of the Berkshire Hills and fifteen minutes drive from Great Barrington, MA, this apartment is located on a secluded seven-acre property. Owners live on the property. Above an artist studio this renovated one bedroom apartment with private entrance, full kitchen, fast internet is stylish, light and airy with a contemporary and eclectic decor. Please note During winter all-wheel drive vehicle is strongly advised.

Top Guest favourite

Guest suite in Canaan

4.98 out of 5 average rating, 350 reviews

Walk to Brewery in Historic Railroad Depot

This light-filled space is in a separate wing of my house with its own private entrance. There is one bedroom with a king-sized bed, spacious living room with table for meals, a large TV, a refrigerator/freezer stocked with bottled water and 1/2&1/2 for coffee, microwave and coffee maker with coffee pods are provided. You will hear the train as it travels through town. There are several places to eat nearby. Be sure to check out GUIDEBOOK on my listing to see what our area offers!!!

Guest favourite

Cottage in New Marlborough

4.94 out of 5 average rating, 122 reviews

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.

Top Guest favourite

Home in Sheffield

4.99 out of 5 average rating, 109 reviews

Belle Meade

Open concept home with a Zen feel and made for relaxation. Nestle into the covered porch and spend hours of peaceful contemplation with nature all around! When you’ve had enough recharging, plan a backroad trip to endless possibilities. Tanglewood and Jacob’s Pillow are nearby via beautiful country roads. There are hikes for any level. Great restaurants, farmer’s markets and Guidos gourmet market just minutes away. Eat out or stay in with a cook’s kitchen and grill deck.

Superhost

Treehouse in New Marlborough

4.92 out of 5 average rating, 131 reviews

Double 3 Bedroom Tree House in the Berkshires

Escape, unwind and recharge in this double treehouse. A live tree runs through the interior connecting you directly with nature while in the comfort of home. Built with refurbished, materials and hand curated with care and love. Feel like you’re in the middle of nowhere, yet it’s only minutes to the town of Great Barrington for shopping dining or just a walk around town. Use these dreamy separate spaces for sleeping, writing or drawing in peace. LGBTQ+ owned and operated.

Guest favourite

Guesthouse in New Marlborough

4.9 out of 5 average rating, 199 reviews

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!

Guest favourite

Home in Great Barrington

4.97 out of 5 average rating, 264 reviews

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.