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 brown hen is seen foraging among the green foliage and fallen leaves. The bird's feathers are a warm shade of brown, blending with the earthy tones of the surroundings. Branches and leaves create a natural frame around the hen.

Loft in Great Barrington

4.99 out of 5 average rating, 334 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.

Guest favorite

An expansive deck is surrounded by lush greenery, featuring outdoor seating and a dining area. Warm café lights hang overhead, creating a cozy atmosphere. A person is seen grilling at a gas grill, while another enjoys a meal at a table, capturing a serene outdoor experience.

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

Guest favorite

A bright and airy living space features a round wooden dining table surrounded by black chairs. Large windows invite natural light, offering views of the scenic outdoor landscape. A seating area with a black sofa is positioned beside a modern fireplace, enhancing the room's comfort.

Apartment in Copake Falls

4.9 out of 5 average rating, 335 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

Top guest favorite

A modern two-story guest house is set amidst a gravel driveway, framed by mature trees and expansive lawns. The building features large windows and a sleek black exterior, allowing for natural light to illuminate the entryway. Soft clouds drift across the sky above.

Guesthouse in Sheffield

5 out of 5 average rating, 17 reviews

Black Bear Bungalow, Sheffield Mass. U Will Love!

This private guest house with full kitchen, living area and large bedroom with Luxurious Queen bed and plenty of storage only 10 miles to Ski Resorts. Sheffield, Mass. is only 5 miles to Great Barrington with wonderful shops, restaurants and grocery stores. You will have a FULL SIZE kitchen in this wonderful guest house. The first level has a full size kitchen, living area with recliners and TV, large bath and laundry. Upstairs is a large bedroom with queen bed. This is a 2 person guest home.

Guest favorite

A wooded dirt road is flanked by lush greenery and trees, leading to a welcoming home visible in the distance. A small, gravel area is situated to the left, suggesting a parking space. Natural light filters through the foliage, creating a serene environment.

Home in Sheffield

4.97 out of 5 average rating, 29 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 serene outdoor space features an inviting fire pit surrounded by gravel pathways and four dark wooden chairs. Soft light from solar lamps illuminates the area, while the surrounding trees create a tranquil natural backdrop.

Cottage in Sheffield

4.94 out of 5 average rating, 156 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

A winter scene is depicted with a red building contrasting against a vibrant sunset sky, filled with shades of orange and pink. Snow covers the ground and rooftops. Dark trees frame the image, contributing to the serene atmosphere.

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.

Top guest favorite

A wooden bowl filled with various eggs sits on a wooden countertop next to a white microwave. A green ceramic pitcher filled with vibrant yellow daffodils adds a fresh touch to the space.

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 favorite

A spacious living area is illuminated by natural light, featuring large windows that offer views of the surrounding trees. Comfortable seating options include a sectional sofa and two round ottomans. A modern dining table for six complements the open layout, creating an inviting atmosphere.

Home in Salisbury

4.99 out of 5 average rating, 69 reviews

Curated Contemporary for lakes, forest & ski hills

Relax in this calm, stylish home, nestled in the foothills of Mt. Washington State Forest on the Mass-CT border. The home is five mins to the bucolic town of Salisbury, 30 mins to all the amenities of the hip town of Great Barrington, and Butternut Ski and Tubing Center. In Summer, you can enjoy farmer's markets, grilling on the wrap-around deck, watersports at 'Twin Lakes'. Hiking can be enjoyed all year round, with access to The Appalachian Trail just 15 mins walk from the property.

Guest favorite

A striking A-frame structure is set among lush greenery, showcasing a blend of wood and stone exteriors. A spacious deck extends from the entrance, framed by a stone pathway, inviting a connection with the natural surroundings.

Cabin in Pine Plains

4.97 out of 5 average rating, 233 reviews

The Upstate A - Modern Luxury in the Hudson Valley

The Upstate A is a 3 bedroom + sleeping loft, 2.5 bathroom A-frame set on a quiet cul-de-sac in the heart of the Hudson Valley. Built in 1968, it was fully renovated in 2020-2021. Staying here you’ll experience a cozy yet modern vibe, immersed in nature but with all the accoutrements of an upscale stay. You'll find great hiking in the summer, skiing in the winter, fresh upstate air year-round and serenity all day and night. See for yourself: check us out on IG @upstate_aframe

Top guest favorite

The image displays a green sign for the Mt. Washington House featuring gold lettering. The sign indicates parking to the right and notes 'No Vacancy.' Wet pavement reflects the surroundings, with a glimpse of greenery and buildings in the background.

Apartment in Hillsdale

4.99 out of 5 average rating, 211 reviews

Serene Suite by Gt. Barrington, Hudson, Tanglewood

Hillsdale’s Hygge Hideaway...Enjoy a peaceful, serene suite with all the comforts of home. Private entrance, with ample parking for multiple cars so you can meet up...perfectly located where the Hudson Valley meets the Berkshires. Just 8 miles east from the Taconic State Parkway, located in the center of the Historic Hamlet of Hillsdale, NY. Walk to unique shops, a cooking school, restaurants and a brewery, a full service grocery store, wine and liquor store and more.

Top guest favorite

Home in Salisbury

5 out of 5 average rating, 50 reviews

Greystone at Twin Lakes

Enjoy a memorable visit when you stay in this unique place. An old family home brought up to 21st century. A short walk down our driveway leads to our camp with 300' of the west shore of Washinee Lake (West Twin Lake). We are 10 miles from Lime Rock Park and Racetrack, close to private schools, and nestled in the beautiful foothills of the Berkshires. Our area enjoys a lush, green Spring and Summer, and spectacular, quintessential New England Fall.