Barn holiday rentals in Massachusetts

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Top-rated barn rentals in Massachusetts

Guests agree: these barn rentals are highly rated for location, cleanliness and more.

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Guest favourite

Cabin in Chesterfield

4.91 out of 5 average rating, 114 reviews

The Glow Room at Indian Hollow

The Glow Room at Indian Hollow is a history-rich 1850 post & beam barn, renovated in a light-filled, post modern style. Imagine getting out of your car, opening the screen door to a big porch that overlooks a leaping mountain brook, deep enough to dunk in. Then pass through the strap-hinged front door and into a glowing pine-panelled great room with giant windows, a big wood stove, 3 Chesterfield couches, dining area and kitchen. You see the forest all around you, but you're inside, ready to unwind. Upstairs, the loft features the master bedroom (sleeps 2, queen) and a reading/games room (can sleep 2, futon). Walking into the ell, you pass the bathroom, the 'room with no purpose,' and the guest bedroom (sleeps 2, futon) which opens onto the back deck, where the barbecue is, and the sound of the leaping waters. In summer the lawn is thick and lush, and you are surrounded with pines, birches, maples and mountains. Chauncey Brook forms the east border & offers a serene and ferny welcome; overlooking it, there's a beautiful firepit surrounded by log benches. The southern border is the Dead Branch Brook with its refreshing plunge pools. About a 1/4 mile downstream it joins the East Branch of the Westfield River, a federally-designated 'Wild and Scenic River.' We will provide you with maps and information about the area, which contains extraordinary opportunities for picnicking, fishing, hiking, biking, swimming, x-country skiing, snow-shoeing, photography and painting. And being alone, with someone you want to be alone with. This property is designed to inspire the maximum enjoyment of the 15+ square miles of open space that begins at its doorstep. The Glow Room is a launching pad. To amplify the quiet and help you unplug, there is no internet service (bring DVDs for your laptop). New cell phones work, but will drop out.

Top guest favourite

Loft in Great Barrington

4.99 out of 5 average rating, 328 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 favourite

Flat in Beverly

4.83 out of 5 average rating, 309 reviews

Salem/Beverly winter get aways and 2025 stays!

Barn by the Harbor! A cozy renovated, shabby chic, barn in historic Beverly is perfect for family visits or coastal exploration. Minutes from Salem, steps from Beverly harbor. Watch the boats while you sip coffee in bed! Enjoy your private patio with a grill. Walk to downtown, the waterfront, beautiful parks or the depot and train to Salem, Boston & Cape Ann. There is a lot to do on the North Shore and there is more to "sea" than Salem! I can give you great ideas! Fun local events all winter!

Guest favourite

Home in Oak Bluffs

4.83 out of 5 average rating, 193 reviews

Waterview, Private, Walk to Beach, Mile to Town

Rustic barn-style home, waterview, spacious natural landscape, serenity, and privacy on 3 acres centrally located 1 mi from Oak Bluffs and Vineyard Haven centers. Walk to beach, bike path nearby, comfortable interiors, memory foam mattresses, cotton linens, 2 HDTVs, high-speed wifi, heat/AC, 2 ocean kayaks, and 2 bikes. Location, amenities and privacy surrounded by natural beauty make staying very easy and relaxing. Ask the host about ferry reservations if they appear to be sold out!

Guest favourite

Guest house in Lenox

4.89 out of 5 average rating, 235 reviews

Modern Barn with Loft at House on Golden Hill

Featuring 35 foot cedar ceilings, large windows, and skylights, The Barn is an oversized two-bedroom apartment with loft at House on Golden Hill, a 1790's farmhouse property in Lenox. The Barn is a detached dwelling with large secluded outdoor space and reserved parking for 3 cars. Situated next to the property's river, the barn provides sweeping mountain views and an idyllic Berkshires experience. Centrally located in the Berkshires and minutes from downtown Lenox and Tanglewood.

Guest favourite

Barn in Holden

4.89 out of 5 average rating, 455 reviews

Farm stay in a Historic Ski Lodge turned Barn

Once a ski lodge, then a horse barn, the hayloft in this unique stone barn has been converted to a comfortable & peaceful getaway. Enjoy a tranquil farm stay on a working Lavender farm. Help feed (if you wish) the sheep and see the horses and chickens. Enjoy the serene views and take in a sunrise or sunset or the stunning evening stars and moon on the back patio, stroll around the farm and hike our 1 mile nature walk. Convenient to local skiing & golfing.

Guest favourite

Guest house in Stockbridge

4.91 out of 5 average rating, 127 reviews

Modern barn in the heart of the Berkshires

Modern, renovated, historic 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.

Top guest favourite

Barn in Williamstown

4.97 out of 5 average rating, 297 reviews

Cozy barn apartment on the river

Private converted first floor barn apartment next to the Green River. Comfortable with unique furnishings and back door that opens to a riverfront covered patio. Sleeps 1-2 comfortably. Can accommodate 4 with the extra sleeper, tri-fold floor mattress, (Best for 1-2 smaller children). Private full bath. Great for 1-2 adults or a family with smaller children. It is on our property with a shared driveway.

Top guest favourite

Flat in Sheffield

4.93 out of 5 average rating, 148 reviews

Private Berkshire Barn Apartment

A private entrance and apartment all to yourself. You are within a 2 minute drive of downtown Sheffield or a 10-15 minute walk. Also within a short drive of superb restaurants and local ski areas, Great Barrington, Tanglewood, Jacobs Pillow, The Rockwell Museum and numerous other Berkshire attractions. Also within a short drive of Berkshire, Salisbury, Hotchkiss and Simon's Rock schools.

Top guest favourite

Barn in Nahant

5 out of 5 average rating, 133 reviews

Entire Beach-Town Cottage, Barn Charm, near Boston

A newly renovated, old barn, fully furnished, where contemporary style meets barn-charm. Located in a quiet neighborhood with private yard and only minutes to the beach. Parking on premises. The ideal location for a short getaway with family or friends or to unwind after a long day at work. Only 25' from downtown Boston and other North Shore towns with restaurants and bars.

Guest favourite

Home in Westport

4.91 out of 5 average rating, 516 reviews

Mermaid Cottage

Relaxing cottage guesthouse near East Branch of the Westport River & Horseneck Beach. Explore winery, brewery, many nature trails, superb biking. Close to Central Village galleries, shopping, Bayside restaurants and Seafood Market at the Town Wharf. Partner's Village Store recommended stop over. Includes High speed Internet, WiFi, Channels Local and LG TV, AC.

Superhost

Home in Cheshire

4.85 out of 5 average rating, 214 reviews

19th c. Barn in The Berkshires

<b> Mason Hill Farm </b> is a celebration of everything we love about the Berkshires. Mountain views, a rushing swimmable brook, an historic restored barn and outbuildings surrounded by lush forest and grazing sheep. Follow us @ <b> mason_hill_farm </b> For weddings & events, please contact us for information on our sister property: Hinterland Hall!