Vacation rentals in Berkshire County

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Top-rated vacation rentals in Berkshire County

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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, 333 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

4.94 out of 5 average rating, 418 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, 334 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 stone archway is framed by lush greenery, leading into a serene garden area. Ferns adorn the foreground, enhancing the natural aesthetic. The rough-hewn stones of the arch display a variety of textures, inviting exploration of the tranquil surroundings.

Treehouse in Tyringham

4.99 out of 5 average rating, 297 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.

Guest favorite

A charming cottage exterior is framed by lush greenery and vibrant flowers. The inviting red door is adorned with a decorative wreath, while large windows display rustic charm. A wooden fence adds an element of privacy, complementing the tranquil setting of this quaint getaway.

Cottage in Great Barrington

4.94 out of 5 average rating, 296 reviews

Artist Cottage

Enchanting, private, romantic, retro style, artsy, cottage & lodge building with fireplaces and outdoor hot tub and shower area in a quaint, quiet, neighborhood nested at the base of Flag Rock and near nature trails and downtown Great Barrington. Perfect for a romantic get-away. Open retro style kitchen with wood stove and TV is stocked with utensils and pans for cooking with gas oven and retro appliances. Upstairs bedroom with ensuite large bathroom with soaking tub and message chair.

Guest favorite

A well-lit hallway is shown, leading towards a staircase with polished wooden steps and a black handrail. A decorative rug is positioned at the entrance, and doors are visible along the walls, adding a sense of depth to the space.

Guesthouse in Great Barrington

4.95 out of 5 average rating, 126 reviews

Sweet Victorian in Housatonic

Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newly renovated Victorian house in Housatonic. Tasteful clean furniture, organic new sheets, pillows and duvets. Lovely clean kitchen that is fully equipped to host dinners. Situated up on a hill in Housatonic this three bedroom is conveniently located to to Great Barrington, Lake Mansfield, Stockbridge, Butternut, Catamount, Tanglewood, Kripalu and Monument Mountain.

Top guest favorite

A wooden sign with the text 'BITTERSWEET FARM' is displayed prominently. Below the sign, a flower bed contains vibrant orange and yellow marigolds, adding a touch of color to the entrance. The surrounding grassy area is well-maintained, enhancing the welcoming appearance of the farm.

Farm stay in Pittsfield

4.99 out of 5 average rating, 222 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.

Guest favorite

A calm lake reflects vibrant autumn foliage, with trees displaying shades of red, orange, and yellow. A boat is anchored near a wooden dock, and the surface of the water mirrors the colorful landscape, creating a serene and picturesque scene.

Cottage in Becket

4.95 out of 5 average rating, 274 reviews

Berkshires Cottage by Lake. Year Round Adventures.

THE BERKSHIRES COTTAGE IN THE WOODS BY A SPRING FED LAKE HAS SOMETHING FOR EVERYONE....... SWIM, FISH, KAYAK, HIKE, SKI, JACOBS PILLOW DANCE FESTIVALS, TANGLEWOOD OUTDOOR CONCERTS, GOLF, DINE, SHOP LEE OUTLETS, DINE WITH ENTERTAINMENT, PLAYS, ANTIQUES, FIRE PITS, HANGING IN A HAMMOCK, FLOAT ON CRYSTAL CLEAR WATER, BBQ ON THE DECK, OR JUST DOING NOTHING AT ALL UNPLUG AND RECHARGE. ESCAPE & RELAX(will consider pets.)(90 second walk through wooded path to lake)

Guest favorite

The exterior of the Granary is highlighted, featuring a mix of red barn siding and natural stone. The two upper windows allow natural light inside, while a mint green double door adds a pop of color. Lush greenery and colorful flowers surround the entrance.

Guesthouse in Lenox

4.93 out of 5 average rating, 376 reviews

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.

Guest favorite

A modern kitchen is featured with stainless steel appliances, a large island, and a mosaic backsplash. An arrangement of fresh orchids and fruit in a bowl adds a touch of nature to the countertop, while abundant natural light floods the space through an arched window.

Home in Great Barrington

4.97 out of 5 average rating, 263 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.

Guest favorite

The kitchenette features modern black cabinetry, open wooden shelves, and a sleek countertop. A microwave and a compact oven are included, along with a sink below a skylight. Glassware, jars, and dishware are neatly arranged along the shelves, enhancing functionality and style.

Guesthouse in Stockbridge

4.95 out of 5 average rating, 234 reviews

Modern studio with views of the treetops

Our Stockbridge studio is located at the heart of the Berkshires, just north of the center of town. It is a new, modern, second floor studio suitable for up to four adults with views of the surrounding woods, a large kitchenette and comfortable, spacious living space for relaxing in your home away from home. There is a full bath and a private entrance. It is perfect for a weekend getaway or a seasonal stay, whatever your heart desires.

Top guest favorite

A circular structure is set in a wooded area, partially surrounded by snow-covered ground. Warm light spills from the open doorway, contrasting with the cool tones of twilight. Trees with bare branches frame the scene, creating a serene winter ambiance.

Apartment in North Adams

4.97 out of 5 average rating, 565 reviews

Steps to MoCA: 2bd + SAUNA!

A large and private 2 bedroom apt at the Small Mansion of Chase Hill, 3 mins by walk to Mass MoCA. 10 mins drive to Williams College, Clark. 5 mins walk to downtown’s restaurants. Whimsically restored (yes, fast Wi-Fi & great water pressure). Part of @chasehillartistretreat YOUR STAY HERE ENABLES US TO HOST REFUGEE/IMMIGRANT ARTISTS PRO BONO!

Vacation rentals for every style

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Cottages

Quaint homes, peaceful surroundings

Chalets

Adventure-ready homes with après-ski style

Popular amenities for Berkshire County vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Berkshire County

Guest favorite

The cozy living area features wooden walls and shelving filled with rustic decor. A large set of windows allows natural light to fill the space, casting shadows on the light-colored floor. A comfortable seating arrangement includes two armchairs and a coffee table, creating a welcoming atmosphere.

Guesthouse in Stockbridge

4.94 out of 5 average rating, 31 reviews

Light-filled Carpenter's Cottage in Stockbridge

EvaRating, 5 stars1 month ago

The house is very comfortable and feels like home. The kitchen is spacious and well-equipped — a great experience for cooking. There’s a peaceful courtyard that’s perfect for calming your mind or reading a book. One night, we even spotted a bear from the window! It’s a great location, and don’t worry — the bears are vegetarian. Elisa and Mickey are very kind and responsive. They’ll even create a personalized list to help you explore the town, even if you’re not familiar with the area. You can shop at Taft Farm — my favorite local farm. Cooking at the house really made it feel like home, and also “farm to table” experience. Thank you!

Superhost

A wooden dock extends over the calm waters of Lake Garfield, featuring two rustic chairs and a small table. Lush trees surround the lake, with a blue sky above dotted with clouds, creating a serene outdoor space for relaxation.

Home in Monterey

4.83 out of 5 average rating, 81 reviews

Rustic 3bd Lake Front Country Cottage

SarahRating, 5 stars1 week ago

Very rustic, private, peaceful kind of like a camp but with air conditioning and excellent wifi. Bald eagle sat over the lake outside. Kayaks were fun. Tons of great hikes and historical things to see. Town of Great Barrington and Sheffield have great antiquing both high and low end. I would go back any time.

Guest favorite

Home in Egremont

4.91 out of 5 average rating, 82 reviews

Modern and Stylish Country Lakeside Cottage

NikiRating, 5 stars4 weeks ago

This was my second time staying at Maureen’s beautiful lakeside home and it surely won’t be my last. It’s the coziest, peaceful and inspiring place. Looking forward to future visits!

Guest favorite

Two black adirondack chairs are positioned on a gravel patio, facing a lush, wooded area filled with trees displaying vibrant autumn foliage. A small wooden table sits between the chairs, creating a serene outdoor space surrounded by nature.

Loft in Austerlitz

4.97 out of 5 average rating, 77 reviews

The Lookout Loft @Moonbeams: stay on 38 acres

StephenRating, 5 stars1 month ago

This small studio above a studio was a perfect oasis for a couple. We highly recommend getting the hot tub! Soaking in the tub while listening to the brook down below was one of the highlights of the trip and just an amazing experience overall. Hosts were super responsive and gave us some great recommendations. The weather was less than ideal but we still had an amazing time - very cozy space and a perfect long weekend getaway.

Top guest favorite

An enclosed three-season porch features large windows that provide natural light and views of the surrounding trees. Comfortable beige seating is arranged around a wooden coffee table, with a modern stove at the center, creating a cozy atmosphere for relaxation.

Home in Great Barrington

4.99 out of 5 average rating, 74 reviews

Stunning luxury home with pool

RochelleRating, 5 stars3 days ago

beautiful well maintained house, supremely functional as well as spacious. very clear instruction all over the house. 5 bathrooms to go with each of 4 bedrooms. multiple lounge areas. fully equipped kitchen with anything once could need.

Top guest favorite

A rustic wooden table, crafted from a solid slab, is paired with matching benches. The table features unique grain patterns and a natural edge, while a bowl of assorted fresh fruits sits at the center. The surrounding area showcases a woven rug and wooden cabinetry.

Cabin in Becket

4.98 out of 5 average rating, 42 reviews

Entire Private Log Cabin in the Berkshires

SharonRating, 5 stars3 days ago

The Becket cottage is secluded and feels like you are up in the trees. The home is comfortable with an awesome screened in porch that we used a lot! It was just the quiet we were looking for in a long weekend. Bob was easy to communicate with - easy instructions and quick replies.

Guest favorite

Two glasses of white wine are placed on a tree stump table, with a bottle of wine beside them. The setting includes rustic chairs arranged around the table, with a flowing river and lush greenery visible in the background.

Tiny home in New Marlborough

4.94 out of 5 average rating, 97 reviews

Cozy Tiny House • Private River & Wood Sauna

ZacheryRating, 5 stars1 day ago

We can’t thank Drew enough. We just spent a night in this tiny home to get away from the city and celebrate our 4th anniversary. The home itself was perfectly pieced together, creating a stress free vibe. The location has prime access to local nature spots (I.e. hiking and waterfalls). Mix that with the great hospitality and amenities (sauna, fire pit, Noble Heart) and there’s really no better cozy getaway. We can’t wait to visit again!

Top guest favorite

The exterior of the Silo Suite is showcased, featuring a distinctive cylindrical design with a metal roof. Surrounding greenery is visible, along with a landscaped pathway leading to the entrance. Comfortable seating is arranged on a wooden deck, inviting relaxation outdoors.

Barn in Williamstown

5 out of 5 average rating, 65 reviews

Silo Suite with Berkshire Mountain Views!

MarthaRating, 5 stars4 months ago

My partner and I booked Sarah's place for a weekend getaway in the Berkshires and had a fantastic stay. Sarah was an incredibly helpful and responsive host and the Silo is the absolute cutest. Would highly recommend and absolutely stay there again.

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Vacation rentals in Berkshire County

Top-rated vacation rentals in Berkshire County

Vacation rentals for every style

Popular amenities for Berkshire County vacation rentals

Other great vacation rentals in Berkshire County

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