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Farmstay vacation rentals in Berkshire County

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Top-rated farmstay rentals in Berkshire County

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Top guest favorite

An exterior view of the renovated red barn features a sloped roof and white-trimmed windows. Two white Adirondack chairs adorned with pink cushions are positioned on the grass, under the shade of a nearby tree, providing a cozy outdoor seating area.

Loft in Great Barrington

4.99 out of 5 average rating, 335 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.

A living area is visible, featuring a sleek gray couch and a modern chair positioned near a stylish fireplace. Artwork is displayed on the wall, and natural light illuminates the space. A neutral rug adds texture to the polished floor, with a bedroom area partially seen in the background.

Apartment in Copake Falls

4.91 out of 5 average rating, 340 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!

A rustic cottage is set against a backdrop of rolling hills and distant mountains. Lush green grass surrounds the property, complemented by well-maintained shrubs. Bright sunlight highlights the exterior, while large windows invite natural light into the cozy interior.

Cabin in Clarksburg

4.9 out of 5 average rating, 289 reviews

Berkshire Mountain Cottage Spectacular Views

This lovely cottage sits on 90 acres featuring gardens, fruit groves, forest, and the Hoosic River. Spectacular views of Mt Greylock. Truly an idyllic location, the perfect retreat for a lover of the outdoors but also close to cultural offerings. Less than 10 minutes to downtown North Adams and Mass MOCA. Williamstown and the Clark Art Institute are nearby as well. Plenty of long or short hikes, scenic walks and bike rides as well as local restaurants and shops that are easily accessible.

A charming stone building is surrounded by lush greenery and colorful flowers, including pink and white blossoms. The sign, featuring 'Stone School Cottage,' is prominently displayed. Large windows indicate a bright interior. The setting offers a peaceful and inviting entrance to the accommodation.

Cottage in Lanesborough

4.93 out of 5 average rating, 247 reviews

Stone School Cottage

Romantic getaway or family vacation. Charming stone building served as a one-room schoolhouse from 1832 until 1950. Beautifully situated amidst horse farms on the scenic road to Mt Greylock, centrally located midway between Williamstown and Lenox. We host lots of writers and musicians who love the bright airy space, families that have fun in this big playhouse, and couples seeking a memorable and private retreat. PLEASE NOTE: this truly-unique building has an unusual layout, described below.

A bright sitting area features a blue sofa adorned with decorative pillows, flanked by two wicker chairs. A wooden dining table is positioned by a large window, providing natural light. Shelves display various decorative items, enhancing the studio's inviting ambiance.

Loft in Great Barrington

4.97 out of 5 average rating, 115 reviews

Studio in Bucolic Berkshire Setting

The 600 Sq. Ft Studio with skylights has a sitting area with sofa-bed, flat screen TV/DVD, sleep area with queen-size bed, dining area, fully equipped kitchen and full bath with shower. Views overlook a 30 acre farm (south) and mountains (east). The studio is in a separate building with a private entrance. The 4 acre property includes perennial and vegetable gardens, an orchard and walking paths. The studio is easily accessible to biking, hiking, swimming, and numerous cultural attractions.

Top guest favorite

A vintage-style freestanding bathtub is filled with water, complemented by a wooden tray featuring a book and a glass of white wine. A soft glow is provided by a candle placed nearby, enhancing the serene atmosphere of the bathroom.

4.99 out of 5 average rating, 160 reviews

Cleveland House - renovated Berkshires' gem.

Enjoy a retreat in a home full of history - it was a tavern/stage coach stop in the 1800's. Today we have added modern comfort while keeping the charm. We are centrally located in the Berkshires making it easy to enjoy -ski Jiminy, hike Mt. Greylock, and enjoy the culture. Or stay in and unwind. Play games on the flat 3-acre yard or try yoga surrounded by nature. Work remotely in our library. Walk down our country road and enjoy the farms. Most of all, reconnect with family/friends.

An open living space features high wooden ceilings with exposed beams and a stylish pool table positioned at the center. A cozy couch sits nearby, with a staircase leading to a loft area visible in the background. Natural light fills the room through large windows.

4.93 out of 5 average rating, 195 reviews

Brooksong, the perfect Berkshires getaway

Part of this bright, sprawling, five-acre property was built in 1866 as a schoolhouse. Its historic charm now includes all the updated comforts of home, in an idyllic country setting that's lovely in all seasons. Located a short drive from Jiminy Peak, Brooksong is perfect for a ski vacation and close to plenty of lakes for summer fun. With a pool table, fire pit, and play set for kids, this is the perfect place to recharge and have fun with the people you care about. Welcome to Brooksong!

A modern tiny house is nestled among tall pines, featuring large windows that invite natural light. A blue door provides access, while a sleek seating area on the deck offers outdoor relaxation. The surrounding forest adds a sense of seclusion and tranquility.

Tiny home in New Marlborough

4.93 out of 5 average rating, 103 reviews

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.

Top guest favorite

A two-story home is depicted, featuring a grey wooden exterior with multiple windows. A wooden deck with stairs leads to the entrance, surrounded by green grass and vibrant yellow flowers. The clear blue sky complements the inviting structure.

Farm stay in Pittsfield

4.99 out of 5 average rating, 242 reviews

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.

A charming shingled farmhouse is surrounded by lush greenery and colorful flowering plants. The stone walkway leads to the welcoming front porch. Tall trees provide shade, while a skylight enhances the natural lighting on the upper level.

Home in Egremont

4.94 out of 5 average rating, 283 reviews

Modern Farm House 5 minutes from Great Barrington

Completely renovated with absolute style, this shingled farmhouse boasts clean modern decor with the architectural charm of a country home. Spacious & sunny kitchen that connects to the large outdoor patio with fireplace. Cozy living room with large flat screen television for streaming Netflix & Amazon. First floor bedroom with bathroom & laundry. The second floor master suite has cathedral ceilings & a jet powered glass shower.

A serene bedroom features a spacious bed dressed in soft linens and a colorful quilt. A cozy couch is positioned against the wall, offering a relaxation spot. Natural light is let in through multiple windows, highlighting the light blue paneled walls and white furniture.

4.97 out of 5 average rating, 107 reviews

Stylish Mid-century Modern Berkshires Cape

Stylish and design forward, yet entirely comfortable for families and kids. Fully renovated 4 bedroom, 2.5 bath home located in the heart of the Berkshires. Enjoy the large, sunny yard and deck with lots of seating and a large dining table - perfect for al fresco dinner and drinks! The house is decorated in mid century modern style with gorgeous design touches throughout!

A rustic red barn stands among lush greenery, featuring large glass doors inviting natural light inside. The path leading to the barn is lined with gravel, and a stack of wood is neatly arranged beside the structure.

Home in Cheshire

4.85 out of 5 average rating, 216 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!

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Popular amenities for Berkshire County farmstay rentals

Free parking on premises

Air conditioning

Family-friendly farm stay rentals

A charming two-story home is nestled among tall trees on a lush green property. The exterior features a light grey facade and a welcoming red roof. Flowers are placed along the pathway, while a deck offers seating, creating a tranquil outdoor space.

Cottage in Hillsdale

4.84 out of 5 average rating, 69 reviews

Secluded Country Getaway on 22 acres

The exterior of the farmhouse is framed by vibrant autumn foliage, featuring a combination of orange, yellow, and red leaves. A gravel driveway leads to the entrance, with a spacious porch that enhances the inviting appearance of the home.

5 out of 5 average rating, 13 reviews

Knoll Rock House (3B/3B) - Best of the Berkshires

An aerial view of Brookside Farm showcases a sprawling single-level farmhouse with a grey shingled roof. Surrounding greenery includes trees exhibiting autumn colors. A gravel driveway leads to the entrance, while a red barn is visible in the background.

4.73 out of 5 average rating, 11 reviews

Large Country farmhouse in the Berkshires.

A bright living area features a comfortable gray sofa and black lounge chairs, arranged around a wooden coffee table. Light streams in through sliding glass doors that open to the backyard. The dining table is visible in the background, surrounded by wooden chairs.

Home in Sheffield

4.94 out of 5 average rating, 33 reviews

Ashley Falls Home w/ Fire Pit: Hike & Ski!

A charming white farmhouse is framed by a decorative white gate adorned with greenery. A pebbled pathway leads to the entrance, surrounded by a well-kept lawn and trees that create a serene, inviting atmosphere.

Guesthouse in Lee

4.85 out of 5 average rating, 40 reviews

1815 Mountainside near Berkshire Theatre Festival

A spacious sectional sofa, adorned with patterned throw pillows, is situated near large windows. A decorative glass coffee table holds several books and a small plate. Warm sunlight filters through the windows, illuminating the cozy seating area.

Apartment in Great Barrington

4.67 out of 5 average rating, 529 reviews

The Treehouse

The farmhouse is framed by neatly trimmed shrubs and a variety of flowering plants. A symmetrical facade features multiple windows that provide natural light to the interior. The surrounding trees and greenery create a peaceful, private setting.

Home in Richmond

4.56 out of 5 average rating, 81 reviews

Josiah Loomis 1832 Homestead

A vibrant rainbow arches over rolling hills, with lush greenery and flowering shrubs in the foreground. Below, the sparkling in-ground pool reflects the surrounding landscape, creating a serene outdoor environment.

Guesthouse in Great Barrington

4.88 out of 5 average rating, 43 reviews

Romantic Berkshires cottage, great views, pool

Farm stay rentals with a patio

A charming exterior of a two-story farmhouse is displayed, featuring a red front door and black-shuttered windows. Lush shrubs flank the entrance, and the surrounding grounds include a manicured lawn and mature trees. The home's siding is white, contributing to its classic aesthetic.

Home in Great Barrington

5 out of 5 average rating, 19 reviews

Elegant 5 Bedroom Farmhouse with expansive lawn

Top guest favorite

The rustic cabin is framed by lush greenery and flowering plants, with a backdrop of rolling mountains under a bright sky. Sunlight casts a warm glow on the weathered log exterior, while picnic tables are positioned on the spacious lawn, inviting outdoor gatherings.

Cabin in Sheffield

5 out of 5 average rating, 31 reviews

The Berkshires Cabin with Stunning Views

A charming two-story farmhouse is set amidst trees, featuring a green metal roof and white siding. A welcoming front porch is visible, flanked by neatly trimmed shrubs. The inviting landscape includes colorful fall foliage and a well-maintained lawn, enhancing the rural setting.

Home in Hillsdale

4.75 out of 5 average rating, 8 reviews

Farm House with valley view

The white farmhouse is set on a lush green lawn, surrounded by tall trees and flowering shrubs. Morning sunlight filters through the leaves, casting gentle shadows on the exterior. The porch invites relaxation with its spacious layout and cozy seating.

5 out of 5 average rating, 6 reviews

Modern NY Berkshires Retreat on 100+ Acres

Top guest favorite

An open dining area features a wooden table surrounded by six antique-style chairs. Large windows allow natural light to illuminate the room, which is adorned with colorful rugs and a cozy couch in the adjacent living space.

5 out of 5 average rating, 26 reviews

4 Bedroom Farmhouse close enough/far enough

A charming house is set on a spacious green lawn, framed by a wooden fence. Surrounding trees add to the natural landscape, with rolling hills visible in the background. The sky displays a mix of clouds, contributing to a serene atmosphere.

4.92 out of 5 average rating, 63 reviews

Mount Greylock View Retreat,3 bedroom,2 1/2 bath.

An outdoor deck features a pair of unique swinging chairs and a dining set under a large umbrella. Lush greenery surrounds the area, with a backdrop of tall trees and a manicured lawn. Colorful lawn furniture is visible in the distance, inviting relaxation.

Home in Hancock

4.95 out of 5 average rating, 37 reviews

Berkshire Retreat: Huge Home W/Hot Tub & Yard

A spacious kitchen features a large wooden island with seating for five. Modern appliances, including a gas stove and coffee station, are positioned among white cabinetry. Natural light floods in through multiple windows, enhancing the bright atmosphere of the inviting cooking space.

Home in New Marlborough

5 out of 5 average rating, 6 reviews

Contemporary Country Farm

Farmstay rentals with a washer and dryer

Top guest favorite

A serene view of rolling hills and lush greenery is framed by a foreground of wildflowers and tall grass. The landscape is dotted with trees, and bright clouds drift across a clear blue sky, creating a peaceful outdoor setting.

Home in Cummington

4.9 out of 5 average rating, 111 reviews

Beautiful Secluded Country House

An old agricultural tool sits in a grassy field, its wheels complementing the expansive landscape. In the background, vibrant hues of sunset illuminate the sky, casting a soft glow over the lush green foliage and distant hills.

Guest suite in Lee

4.72 out of 5 average rating, 199 reviews

Berkshire Charm w/ Panoramic views

The entrance to River Cottage is framed by lush hydrangea plants filled with clusters of pale green flowers. A welcoming door is positioned at the center, with a striped mat lying on the steps and a wooden chair positioned to one side.

Home in Great Barrington

4.96 out of 5 average rating, 50 reviews

River Cottage: Riverfront Home, Walkable Community

The exterior of a renovated antique farmhouse is displayed, featuring a white facade and multiple entrances framed by greenery. A spacious lawn surrounds the house, complemented by mature trees in the background under a clear blue sky.

Home in Lanesborough

4.9 out of 5 average rating, 111 reviews

Elmwood Farmhouse

Top guest favorite

The exterior of a two-story, white house is framed by lush greenery and flowering shrubs. A walkway leads to the front porch, where two potted plants are placed. The roof is dark and the house is adorned with prominent blue shutters, creating a welcoming facade.

4.99 out of 5 average rating, 81 reviews

Mountain Escape: book Fall Color & Ski Season now!

A spacious living area is highlighted by exposed wooden beams and hardwood flooring. A large sectional sofa faces a rustic fireplace, which is surrounded by logs. Natural light enters through multiple windows, illuminating the cozy ambiance.

Cottage in Becket

4.77 out of 5 average rating, 167 reviews

Tranquil Lake Cottage on 3 Acres with Large Deck

An outdoor scene features a clear blue sky above a heated saltwater pool set within a spacious green yard. Surrounding trees provide a natural backdrop, and a small shed is visible next to the pool, which is enclosed by a wooden fence.

Home in New Lebanon

4.98 out of 5 average rating, 62 reviews

Berkshire Mountain home views, pool, Queechy Lake

The historic farmhouse stands gracefully on a large grassy lawn, surrounded by trees showcasing autumn foliage. The structure features a distinct architectural design with a prominent front porch and several windows reflecting the natural light.

Farm stay in Stephentown

4.92 out of 5 average rating, 12 reviews

*Jericho Hollow Farm* 5 Minutes to Jiminy Peak

Destinations to explore