Vacation rentals in Race Brook Falls

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Top-rated vacation rentals in Race Brook Falls

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Top guest favorite
A striking octagonal home is illuminated at dusk, showcasing wrap-around glass windows that blend with the surrounding woodland. The exterior features natural stone accents, and a warm glow from a light at the entrance creates a welcoming ambiance amidst a snowy landscape.
Chalet in Otis
4.95 out of 5 average rating, 482 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 favorite
Loft in Great Barrington
4.99 out of 5 average rating, 368 reviews

The Old Red Barn

Renovated studio in barn built circa 1830, centrally located to all activities in the Berkshires. Bright and sunny space with views of fields and spectacular sunsets. Open upstairs loft bedroom with pine floors, catherial ceiling, exposed beams, full kitchen , bathroom and washer and dryer. The Berkshires are beautiful in the fall , come stay ! 5 minute drive to town. Walk to the Green River , hike the trails. We provide all basic household supplies. We invite all to enjoy our old red barn.

Top guest favorite
Cabin in Mount Washington
5.0 out of 5 average rating, 13 reviews

Chic Cabin in the Berkshires, Mountain getaway!

Find serenity at this cozy cabin set on ten tranquil acres at the end of a dead end road on top of Mt Washington, Massachusetts. This chic cabin is a private, peaceful oasis in the woods. You will find yourself very near the benchmark of Massachusetts, Connecticut and New York with endless hiking trails right outside your door, including The Appalachian trail. You will be at the doorstep of all the culture, shopping and dining that the Berkshires, Litchfield and Columbia County have to offer.

Guest favorite
The image captures a vibrant garden filled with blooming flowers in various shades. A grassy area leads to a rustic red house nestled among trees, providing a serene and inviting environment. Several large bushes contribute to the lush greenery surrounding the property.
Home in Sheffield
4.98 out of 5 average rating, 55 reviews

Bull Hill Bungalow

Relax with the whole family at this peaceful, cozy home. Set on five acres located in the lovely Berkshires. Walk, bike, and hike the trails, ski Butternut and Catamount, rent a pontoon boat at nearby Twin Lakes, and explore the many great restaurants in Great Barrington and Salisbury. Immerse yourself in the culture. Tanglewood, Jacobs Pillow and many theaters are nearby. When in season, you can pick fresh vegetables from the garden, fruit from the fruit trees, and berries from the bushes.

Guest favorite
A spacious kitchen is equipped with white cabinetry and a large wooden island, featuring bar seating. Natural light floods the room through multiple windows. A dining table for six complements the space, with a fruit bowl as a centerpiece.
Cottage in Sheffield
4.92 out of 5 average rating, 192 reviews

Cheerful 3-bedroom cottage with woodstove.

Relax with the whole family at this peaceful Berkshire getaway with easy access to all the area has to offer. A quick 20-minute drive to Butternut or Catamount ski hills, as well as downtown Great Barrington. Tanglewood and Jacob's Pillow are a half-hour's drive. Or stay at home and enjoy the peace and quiet of the surrounding woods, light a fire in the woodstove, cook in the large fully-equipped kitchen or head out back to barbecue on the large deck and play a game of badminton in the yard.

Top guest favorite
Home in Lee
4.99 out of 5 average rating, 313 reviews

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.

Top guest favorite
Home in Sheffield
4.96 out of 5 average rating, 28 reviews

Family friendly house with fenced yard & fire pit

Hillside Haus is a modern house close to Catamount Mountain & Ski Butternut and Hotchkiss School. Enjoy high ceilings, a cozy fire pit, fenced yard, family-friendly amenities (including crib and high-chair), and fully stocked kitchen. Sleeps 6 comfortably, and includes an office space. Perfect for year-round getaways—ski in winter, hike and picnic at nearby lakes and campgrounds in summer. Quick drive to charming and vibrant Great Barrington for shopping, art, and restaurants.

Top guest favorite
A modern farmhouse bungalow is nestled among lush greenery along a brook. The red exterior is complemented by white trim and a front porch. A wooden bench sits by the water's edge, inviting relaxation amidst the tranquil natural surroundings.
Bungalow in Egremont
4.99 out of 5 average rating, 138 reviews

3-bedroom Berkshire bungalow on 2.5 peaceful acres

Modern farmhouse bungalow with private bridge and brook! Offering privacy as well as nearby nightlife, set upon 2.5 acres of beautiful Berkshire landscape but only 7 minutes to downtown Great Barrington and a short drive to Catamount and Butternut ski area. Mountains, waterfalls, countless hikes and bike routes, farmers' markets, coffee shops, breweries, Shakespeare and Co, Tanglewood, and world-class restaurants all come together in this quintessential New England community.

Guest favorite
The treehouse is nestled among tall trees, surrounded by a gravel area. A cozy seating arrangement with several chairs is positioned near a fire pit, offering an inviting outdoor space. A shaded canopy provides shelter, enhancing the serene forest setting.
Treehouse in New Marlborough
4.91 out of 5 average rating, 171 reviews

Berkshire Treehouse Retreat

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 favorite
Tiny home in New Marlborough
4.94 out of 5 average rating, 191 reviews

Bedroom Forest View I Sauna I Fire-pit I Trails

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, 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.

Guest favorite
A bright living area is featured, showcasing large windows that provide views of the surrounding nature. A fireplace is positioned centrally, complemented by a light-toned wooden sofa and a cozy chair. A dining table for two is visible, along with a small shelf and potted plants.
Cottage in Great Barrington
4.94 out of 5 average rating, 219 reviews

The Cottage at The Barrington House

Welcome to the Cottage at the Barrington House! The Barrington House is nestled in the serene Berkshires Mountains - which have long been a sanctuary for weary city dwellers seeking breathing space, a perfect retreat for artists, writers and thinkers! It's sprawling grounds offer stunning views of lush valleys and distant peaks, while the interior features a fireplace, cozy reading nook, and unlimited windows that invite the natural world inside.

Top guest favorite
A charming cottage is framed by vibrant flowering shrubs and greenery. The front porch is adorned with decorative elements, while large windows invite natural light into the space. A wooden fence encloses the front garden, enhancing the quaint and inviting atmosphere.
Cottage in Great Barrington
4.93 out of 5 average rating, 351 reviews

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.

Popular amenities for Race Brook Falls vacation rentals