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House holiday rentals in Berkshire County

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Top-rated house rentals in Berkshire County

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Home in Becket

Lake front retreat - Stylish Berkshire home

Experience total privacy at this beautiful mid-century home with 4 bedrooms on Long Bow Lake. Featuring stylish wood floors & modern design, the cozy dining room boasts a gas fireplace. This family-friendly getaway offers exclusive lake frontage, complete with a dock & 4 kayaks for endless adventures! Enjoy serene moments on the screened porch, fire up the Weber grill, or challenge each other to ping pong. Just 15 minutes from Downtown Lee, close to outlets, hiking trails, and Otis Ridge skiing!

4.92 out of 5 average rating, 181 reviews
Guest favourite
An open living area showcases rustic wooden beams and a cozy gas fireplace. A modern gray sofa faces the fireplace, complemented by a glass coffee table with a vase of pink flowers. Natural light floods in from the glass doors, leading to the lush green outdoor space.
Home in Stockbridge

Bright Stockbridge country home, near everything!

Berkshires charm in this fully renovated 1800's post and beam farmhouse set on 5 park-like acres. Features open plan living/dining/kitchen with gas cooktop and gas 3 sided fireplace, lovely sun room, master suite downstairs and 2 br, bath and sitting area upstairs. Spacious deck overlooking the expansive property Conveniently located between the charming towns of Stockbridge, Lenox & Great Barrington. We are surrounded by 4 ski areas, the closest is 10 minutes away! Many dining options too.

4.95 out of 5 average rating, 191 reviews
Top Guest favourite
A charming outdoor seating area is situated under a spacious pergola, designed with warm lights. Comfortable seating is set on a stone patio, with a grill nearby, surrounded by a grassy yard. Soft clouds and a gentle twilight sky provide a serene backdrop.
Home in Lee

Berkshire 4 season home

The house is located in the heart of the Berkshires. It's less than 10 miles from Tanglewood, Kripalu, Jacob's pillow Dance, Monument Mountain, Beartown state forest, Norman Rockwell Museum, Shakespeare & Co., Ski Butternut, Lee Prime outlets. Located 1.5 miles from the turnpike exit for easy travel, 3 miles from Laurel lake, walking distance to a public golf course and downtown Lee where you will find great restaurants. There is Cable internet that is fast and reliable if you have to work.

4.98 out of 5 average rating, 253 reviews
Top Guest favourite
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.
Home in Dalton

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!

4.93 out of 5 average rating, 212 reviews
Guest favourite
A bright living area features a yellow couch and two accent chairs, inviting relaxation. A patterned area rug centers the space, while natural light filters through large windows. A staircase is visible in the background, along with decorative plants and artwork adorning the walls.
Home in Pittsfield

Cantabile life in the Berkshires

Relax with your family and friends after a day of skiing, hiking or a night of Tanglewood concert in this newly renovated home at the center of the Berkshires. Located in a quiet and friendly neighborhood, our home is 5min to Pontoosuc Lake and Lake Onota, 10min to Bousquet, 15min to Mt Greylock, 20min to Jiminy Peak and Tanglewood. Multiple grocery stores and shopping centers near by. Child/baby friendly, we have books, games, PingPong, foosball and a grand piano. Musicians are welcome!

4.95 out of 5 average rating, 240 reviews
Guest favourite
A spacious living area features a modern sectional sofa adorned with various cushions, positioned around a round coffee table. Exposed wooden beams and high ceilings create an open atmosphere. A staircase leads to an upper level, and natural light illuminates the well-equipped kitchen visible in the background.
Home in Lee

Stonebridge Cabin: Modern Amenities, Enjoy Nature!

Our quiet, peaceful and nestled in the woods, is a meticulously updated modern retreat offers the quiet comfort of a home away from home. Only 5 minutes from town and in the heart of the Berkshires, this cozy cabin is a perfect escape from everyday life. Enjoy the fully appointed trappings of modernity—high-speed internet, a beautifully updated and well-stocked kitchen, hot tub, brand new stylish and comfortable furnishings, TV room, and more! Find us on social media: @stonebridgecabin

4.88 out of 5 average rating, 108 reviews
Top Guest favourite
A quaint lakeside cottage features large windows for scenic views and a deck with outdoor seating. A grill is positioned nearby for easy outdoor cooking. The property is framed by lush greenery, enhancing the natural setting by the water's edge.
Home in Becket

Cozy lakehouse

Relax with family or friends at this sweet cottage on Center Lake in the Berkshires. This lakeside cottage is charming and rustic. Enjoy a beautiful day on the lake swimming, fishing off the dock and kayaking. Grill dinner on your private deck and watch the stars come out in the evening Or enjoy all that the Berkshires have to offer, Jacob’s Pillow (15 min), Berkshire Theater (20 min), Tanglewood (30 min). There are plenty of nearby hiking trails and charming towns to explore.

5.0 out of 5 average rating, 119 reviews
Guest favourite
Home in Becket

HOT TUB! Dog & Family Friendly in the Berkshires!

Secluded Berkshires Retreat! -Dog/s, Family Friendly cottage -Freshly painted & new floors for 2026! -Patio w/ Hot tub, fire pit, canoe use -Acre secluded lot -Historic Lee, Stockbridge, Lenox/Tanglewood, Norman Rockwell Museum w/in 30 min! -30 min Monument Mt. & Berkshires Scenic Railway -Appalachian Trail hiking -Naumkeag Pumpkin Show/Christmas Lights -Wineries/Breweries -Outlets/Small Shops -Master w/Queen -2nd bed with 1 Twin/Full Bunk -Full size pull out couch

4.93 out of 5 average rating, 136 reviews
Top Guest favourite
Home in Monterey

Beautiful family home, Hike, Fireplace, Sleeps 12

Voted by Airbnb guests as a top "Wish-listed family home" * A beautiful 5 bedroom post & beam house in the woods off the Appalachian trail. * Butternut ski Mountain 15 mins * Roaring fireplace & free firewood * Outdoor fire pit * Great Hikes from the house * Pets welcome * Fast Wifi - Fiber * Great Barrington 15 mins/ local shops * Kids activities at the house & area. * Jacobs Pillow & Tanglewood 20 mins * Fishing, kayaking & Swimming Lake 5 mins

4.96 out of 5 average rating, 237 reviews
Guest favourite
The spacious living room features large windows that provide scenic views of the mountains and lake. A comfortable sectional sofa is complemented by a decorative throw and cushions. The ceiling is elevated with wooden beams, and stylish decor enhances the inviting atmosphere.
Home in Monterey

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.

4.96 out of 5 average rating, 311 reviews
Top Guest favourite
The tranquil lake reflects a soft sunrise, showcasing a palette of warm hues and gentle ripples. A dock and small boats are visible on the water, framed by the serene landscape of trees along the shore.
Home in Otis

Idyllic family retreat - spacious lake home,

This recently renovated waterfront home is perfectly situated close to many Berkshire attractions for an ideal getaway. Lake views are stunning year around. The fire-pit at shore offers a unique outdoor gathering option. Warm and welcoming interior with three levels of living for families and friends (up to 8 people). Area offers family-friendly hiking. Enjoy the whimsical decor and mid-century style furnishings. Cook in the well-equipped kitchen.

4.95 out of 5 average rating, 176 reviews
Top Guest favourite
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.
Home in Lee

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!

4.97 out of 5 average rating, 143 reviews

Popular amenities for Berkshire County house rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favourite
The exterior shows a modern home embraced by lush greenery. A wooden deck with a railing wraps around the entrance, complemented by well-maintained landscaping featuring shrubs and plants. Trees provide a natural backdrop, enhancing the tranquil rural setting.
Home in Pittsfield

Berkshire Getaway Ranch 3 acres + saltwater pool

4.93 out of 5 average rating, 109 reviews
Guest favourite
A comfortable living room features a large sectional sofa and a wooden coffee table. A reclining chair is positioned nearby, while a flat-screen TV is mounted on the wall. Natural light enters through glass doors, which open to the outdoor area. Soft colors and warm tones create a cozy ambiance.
Home in Lee

Berkshire Vacation Home in Lee

4.93 out of 5 average rating, 106 reviews
Top Guest favourite
A pathway lined with lush greenery leads to a bungalow with a screened-in porch, featuring outdoor seating. The soft sunlight filters through the foliage, creating a serene entrance to the welcoming space.
Home in Williamstown

Hollywood Bungalow in the Berkshires #C0191633410

4.9 out of 5 average rating, 242 reviews
Top Guest favourite
A bright living room is highlighted by a grand piano and a modern gas fireplace, both set against a light brick wall. Large windows provide natural light, and wooden flooring adds warmth. A comfortable dark sofa and armchairs are arranged around a glass coffee table.
Home in Great Barrington

Stunning luxury home with pool

4.99 out of 5 average rating, 95 reviews
Top Guest favourite
A spacious open-plan living area is showcased, featuring large windows that invite natural light. A modern sectional sofa in warm tones is arranged around a low table. A dining area with a long table and dining chairs is visible in the background, enhancing the inviting atmosphere.
Home in Egremont

The Catamount Ski Haus with Pool & Hot Tub

5.0 out of 5 average rating, 73 reviews
Guest favourite
Home in Great Barrington

Farmhouse Retreat • Hot Tub • Fireplace • Ski

4.93 out of 5 average rating, 15 reviews
Guest favourite
Home in West Stockbridge

Modern Log Cabin w/Pool & Views By Evergreen Home

5.0 out of 5 average rating, 13 reviews
Top Guest favourite
A large, inviting pool is framed by lounge chairs, offering ample seating for relaxation. The pool reflects the cloudy sky and surrounds are well-maintained. The house is visible in the background, featuring a bank of windows that overlooks the serene lake landscape beyond.
Home in Pittsfield

Berkshire Lakefront Home W/Pool-100%Renovated

4.98 out of 5 average rating, 85 reviews

Weekly house rentals

Top Guest favourite
Home in North Adams

Steps to MoCA private house + SAUNA!

4.98 out of 5 average rating, 561 reviews
Top Guest favourite
The kitchen features light-colored cabinetry with black hardware, complemented by a wood countertop. A refrigerator and an oven with a stovetop are included. A dining table with light wooden chairs is positioned nearby, and a rug adds texture to the hardwood flooring.
Home in Great Barrington

Prime location for the best of the Berkshires

4.97 out of 5 average rating, 141 reviews
Guest favourite
A wrap-around porch features a small table with two colorful chairs, overlooking a serene lake framed by lush trees and greenery. The view showcases calm water, complemented by distant hills under a clear blue sky.
Home in Canaan

Berkshire Lakefront House with Amazing Views

4.91 out of 5 average rating, 188 reviews
Superhost
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

19th c. Barn in The Berkshires

4.85 out of 5 average rating, 230 reviews
Guest favourite
A striking black chalet with a stone chimney is framed by snow-covered trees. The spacious deck features multiple outdoor seating areas, offering views of the surrounding winter landscape, while large windows provide ample natural light to the interior.
Home in Becket

Lakefront Retreat | Dock, Kayaks & Fire Pit

4.94 out of 5 average rating, 110 reviews
Top Guest favourite
Home in Pittsfield

Cozy cottage on peaceful pond

5.0 out of 5 average rating, 38 reviews
Top Guest favourite
The exterior of a transformed church features a pointed steeple and a central double door framed by a decorative arch. Stained-glass windows are visible, adding a historic charm against the dark wood siding. The surrounding area is lined with trees, hinting at the serene natural setting.
Home in Great Barrington

Berkshires Black Abbey

5.0 out of 5 average rating, 47 reviews
Top Guest favourite
Home in New Lebanon

Modernized 1860s Getaway w/ Queechy Lake Passes*

5.0 out of 5 average rating, 28 reviews

Private house rentals

Top Guest favourite
An outdoor area features a wooden barrel sauna alongside a modern hot tub. The hot tub's white surface contrasts with the natural wood of the sauna, set against a backdrop of lush green trees and a wooden fence, creating a serene environment for relaxation.
Home in Great Barrington

Sauna + Hot Tub Escape | Private & Pet Friendly

5.0 out of 5 average rating, 56 reviews
Top Guest favourite
A charming house is nestled among autumn foliage, displaying warm earthy tones. A winding stone pathway leads to the entrance, framed by a well-maintained stone wall and lush greenery. Colorful leaves adorn the surrounding trees, creating a serene and inviting landscape.
Home in Great Barrington

Seekonk Hill

4.98 out of 5 average rating, 48 reviews
Top Guest favourite
An open living and dining area features a wooden ceiling with a skylight and large windows providing natural light. A stylish dining table with chairs sits in the foreground, while a cozy seating arrangement is visible to the side, complemented by a fieldstone fireplace.
Home in West Stockbridge

Secluded Chic Mountain Chalet near Tanglewood

4.93 out of 5 average rating, 58 reviews
Top Guest favourite
Home in Great Barrington

RENOVATED BERKSHIRE COUNTRY CASTLE

4.97 out of 5 average rating, 58 reviews
Top Guest favourite
A spacious kitchen area is presented with light-colored cabinetry and a modern countertop. A wooden table, designed to accommodate ten, is centered in the room. Open shelves display glassware, and stainless steel appliances are visible, enhancing the functional layout.
Home in Lenox

Home away from home: Minutes to Tanglewood.

4.93 out of 5 average rating, 61 reviews
Guest favourite
A bright living room features a comfortable white sofa and a plush armchair beside a coffee table on a patterned rug. Large windows allow natural light to illuminate the space, while a television is positioned against a wooden accent wall. A potted plant adds a touch of greenery.
Home in Lee

Spacious Central Berkshires Home for Groups

4.89 out of 5 average rating, 56 reviews
Top Guest favourite
An open living area features cathedral ceilings supported by wooden beams. A mix of bright furniture includes a yellow sofa and a red sectional. Large windows allow ample natural light, illuminating the wooden floors. A cozy wood stove complements the inviting space.
Home in Stockbridge

Secluded Family Home in Serene Stockbridge Woods

4.99 out of 5 average rating, 88 reviews
Top Guest favourite
Home in Sheffield

Family friendly house with fenced yard & fire pit

4.97 out of 5 average rating, 32 reviews

Destinations to explore