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House vacation rentals in Berkshire County

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Top-rated house rentals in Berkshire County

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

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Guest favorite
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, 188 reviews
Top guest favorite
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, 249 reviews
Top guest favorite
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, 211 reviews
Top guest favorite
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, 232 reviews
Guest favorite
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

Enjoy the culture of the Berkshires & Hudson - 15 min from Tanglewood, Norman Rockwell Museum, Shakespeare & Co, PS21, McHaydn Theatre, Mount Greylock, Jiminy Peak Resort, zipline parks, Bousquet & more. Restaurants & market within driving distance and a membership-only beach within a short walk or drive. Great lake views with wrap-around porch. The lake is family-friendly. We welcome couples, solo adventurers, and families. Sorry, no "Group Bookings" - book & pay via one account only.

4.91 out of 5 average rating, 187 reviews
Top guest favorite
Home in Lee

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

4.99 out of 5 average rating, 318 reviews
Top guest favorite
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, 116 reviews
Top guest favorite
A serene bedroom is presented with a spacious bed adorned with soft linens and a cozy throw. Two bedside tables hold elegant lamps, and natural light floods the room through large windows. A decorative wreath hangs above the headboard, enhancing the tranquil ambiance.
Home in Sheffield

Belle Meade

Open concept home with a Zen feel and made for relaxation. Nestle into the covered porch and spend hours of peaceful contemplation with nature all around! When you’ve had enough recharging, plan a backroad trip to endless possibilities. Tanglewood and Jacob’s Pillow are nearby via beautiful country roads. There are hikes for any level. Great restaurants, farmer’s markets and Guidos gourmet market just minutes away. Eat out or stay in with a cook’s kitchen and grill deck.

4.99 out of 5 average rating, 133 reviews
Top guest favorite
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, 233 reviews
Top guest favorite
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, 309 reviews
Top guest favorite
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, 175 reviews
Guest favorite
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 -Wineries/Breweries -Outlets/Small Shops -Master w/Queen -2nd bed with 1 Twin/Full Bunk -Full size pull out couch

4.94 out of 5 average rating, 134 reviews

Popular amenities for Berkshire County house rentals

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favorite
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, 108 reviews
Top guest favorite
A serene view features a private in-ground pool surrounded by lounge chairs, each shaded by black umbrellas. Lush green trees border the backyard, and a red house is visible in the background, completing the outdoor vacation atmosphere.
Home in Canaan

Berkshire Lake House, gunite pool, Chef's Kitchen

4.99 out of 5 average rating, 101 reviews
Top guest favorite
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, 239 reviews
Guest favorite
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, 105 reviews
Top guest favorite
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
Top guest favorite
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, 94 reviews
Guest favorite
Home in West Stockbridge

Modern Log Cabin w/Pool & Views By Evergreen Home

5.0 out of 5 average rating, 11 reviews
Top guest favorite
Home in Great Barrington

Fall Foliage @ The Barrington House: GB

5.0 out of 5 average rating, 17 reviews

Weekly house rentals

Top guest favorite
Home in North Adams

Steps to MoCA private house + SAUNA!

4.98 out of 5 average rating, 555 reviews
Top guest favorite
A spacious living room features a dark sectional sofa and a wooden coffee table on a light rug. A modern armchair is positioned nearby, with a floor lamp providing light. Large windows allow natural light and offer views of the surrounding trees.
Home in Lanesborough

Tranquil mid-century modern Berkshires retreat

4.99 out of 5 average rating, 135 reviews
Top guest favorite
A charming two-story red house is surrounded by lush greenery and colorful flowering plants. Sturdy steps lead up to the entrance, framed by vibrant shrubs and hydrangeas, creating a welcoming outdoor area that blends naturally with the landscape.
Home in New Lebanon

The old sawmill from 1771

4.99 out of 5 average rating, 385 reviews
Top guest favorite
The charming exterior of a renovated farmhouse features a spacious front porch with a red bench and hanging flower baskets. Large windows allow natural light to fill the entryway, while lush green grass and trees frame the property.
Home in Canaan

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove

4.99 out of 5 average rating, 119 reviews
Top guest favorite
The charming farmhouse features a covered porch with seating, surrounded by a vibrant garden filled with colorful flowers. Solar panels are visible on the roof, while a grassy area and a small fire pit enhance the outdoor space, inviting relaxation in a natural setting.
Home in Great Barrington

Walk to Town! Great Barrington 4-bedroom farmhouse

5.0 out of 5 average rating, 116 reviews
Guest favorite
An entryway features a grey console table with glass-front cabinets, topped by a table lamp and a potted plant. A round mirror hangs above the table, while a doorway leads into the home, revealing glimpses of the kitchen and hallway beyond.
Home in Stockbridge

Sun-filled, Charming Stockbridge Classic- In Town!

4.94 out of 5 average rating, 167 reviews
Top guest favorite
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, 140 reviews
Guest favorite
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!

4.88 out of 5 average rating, 108 reviews

Private house rentals

Superhost
Home in Monterey

Forget-Me-Not by AvantStay | Bold Lakefront Escape

4.9 out of 5 average rating, 70 reviews
Top guest favorite
An aerial view of a lakeside home surrounded by trees showcasing fall foliage. A wooden dock extends into the calm water, with the house positioned amidst lush greenery. The vibrant autumn colors add warmth to the natural setting.
Home in Becket

Fall Foliage Lakefront Retreat - Berkshires

5.0 out of 5 average rating, 46 reviews
Top guest favorite
A serene lakefront property is viewed from the water, featuring a well-maintained lawn and inviting home. The structure is flanked by mature trees, while a small private dock extends into the lake, providing easy access to the water.
Home in Lanesborough

Lakefront Home on Ponstoosuc Lake, The Berkshires

5.0 out of 5 average rating, 26 reviews
Top guest favorite
Home in Lenox

The Berkshire Quintessential Cape downtown Lenox

5.0 out of 5 average rating, 7 reviews
Top guest favorite
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
Guest favorite
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, 53 reviews
Top guest favorite
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 favorite
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, 58 reviews

Destinations to explore