House holiday rentals in Great Barrington

An aerial view showcases a serene lake bordered by lush greenery and trees, with the elegant cottage nestled among them. A private dock extends into the calm waters, reflecting the surrounding nature. The expansive landscape emphasizes the cottage's tranquil, waterfront location.

4.96 out of 5 average rating, 186 reviews

Elegant Year-Round Lakeside Retreat with AC

The Haven, an elegant cottage surrounded by woods, located on a pristine lake with private dock. 4 bedrooms, 3 baths. This year-round vacation cottage with hot tub provides an experience in the Berkshires you won’t forget! Leaf-peep in fall, ski in winter, hike in spring, kayak & swim in summer, or browse the boutique shops in quaint towns like Great Barrington, Lenox and Stockbridge. Newly installed mini-splits provide AC in all bedrooms and LVR/DR/Kitchen common area. 1 house-trained dog ok.

A hot tub sits on a polished wooden deck, surrounded by greenery. Soft lighting from string lights illuminates the area. A colorful striped pillow rests on a lounge chair, with a patterned plate and drink placed nearby, creating a relaxing outdoor retreat.

4.95 out of 5 average rating, 130 reviews

Best of the Berkshires + Hot Tub by Evergreen Home

10 MINUTES TO CATAMOUNT Ski, hike, shop, and dine with this beautiful 2-bed, 1-bath Berkshires cottage as your home base. 7 minutes to downtown Great Barrington, this stylish, cozy rental has everything you need for a great getaway. A new renovation brings modern amenities to this classic 50’s cottage. Enjoy a chef’s kitchen, 500 sq-foot deck with hot tub, and thoughtful touches like yoga mats, a record player, board games, and a backyard hammock. Monthly ski rental discounts are available!

4.95 out of 5 average rating, 154 reviews

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.

4.94 out of 5 average rating, 297 reviews

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

Modern Farm House 5 minutes from Great Barrington

Completely updated with style, this shingled farmhouse combines modern decor with the charm of a country home. Enjoy a spacious, sunny kitchen that connects to a large outdoor patio featuring a fireplace. The cozy living room has a large flat-screen TV for streaming. The first floor includes a bedroom with an attached bathroom & laundry. The second floor suite boasts cathedral ceilings a luxurious jet-powered shower. This home offers a perfect blend of comfort and elegance for your stay!

The living room features a spacious leather sectional sofa facing a TV, with a wooden coffee table placed in front. A wood stove is positioned nearby on a black hearth, and a large window allows natural light to illuminate the space, adorned with plants and decorative items.

4.9 out of 5 average rating, 273 reviews

Cozy Berkshires Cottage

Stay in a cozy, newly remodeled Berkshires 1920's cottage! We've added bedrooms and a bathroom with a soaking tub upstairs, expanded the first floor bathroom and added a laundry room. The cottage is set back from the main road, easily accessible yet private. -Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. -Ideal for couples, adventurers, business travelers, and furry friends (pets). -Note: Stairs to the 2nd floor are steep: guests are responsible for child safety.

4.94 out of 5 average rating, 107 reviews

A light-filled bedroom features a white bed with plush bedding, complemented by two windows covered with dark blinds. A small nightstand holds a lamp, and a wooden chair adds to the decor. The walls are adorned with framed photographs.

Home in Sheffield

Great Berkshire Getaway !

"238 Main" has two rentals. Only one rental is rented at a time. Rental #2 has a Queen size bed, FULLY EQUIPPED KITCHEN and is SUPER CLEAN! (SEE THE TWO BEDROOM LISTING #1) We are conveniently located between Butternut and Catamount ski stations. Fully renovated with private garden, entrance, terrace and parking. Queen size bed. Hi Speed Wifi. Bathroom has radiant floor heat, towel warmer, plush bathrobes, hair dryer and toiletries. In the heart of the Berkshires! Come visit!

4.99 out of 5 average rating, 121 reviews

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, 306 reviews

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 relax by the firepit- we hope you enjoy your stay and will visit us again.

Superhost

The exterior of a two-story yellow house is presented, featuring a front porch with large windows and a central door. A water tower is visible in the background, surrounded by greenery and a gravel pathway leading to the entrance.

Home in Housatonic

4.7 out of 5 average rating, 125 reviews

Relaxing Housatonic Retreat

This home is where my husband grew up and has been in his family for many years. It's currently my father-in-law's summer house and is in various stages of updating. The village of Housatonic is one of our favorite places on Earth! With quaint restaurants within a five minute walk, hiking trails nearby, spectacular foliage in the fall, and several ski areas to choose from, it has something for more active people or those who would just like a quiet, relaxing retreat.

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.

5 out of 5 average rating, 104 reviews

Walk to Town! Great Barrington 4-bedroom farmhouse

Enjoy the yard and garden at this charming 4-bedroom in-town farmhouse. The garden features various fruits and vegetables in season. Stroll to Great Barrington's restaurants and shops. Hike the woodland trail up the hill for a swim at nearby Lake Mansfield. Retreat to the private garden hideaway. This place has something for everyone who wants to relax in a cozy setting yet still be near everything Great Barrington has to offer.

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, 121 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. 15 minutes from Butternut ski to south + Bousquet to the north, 35 min to Jiminy Peak. Cozy up by the wood burning fireplace and enjoy the winter wonderland! The house is decorated in mid century modern style with gorgeous design touches throughout!

A light-filled open living area features a large sectional sofa arranged around a coffee table, with a soft rug underfoot. Two expansive windows provide views of the greenery outside. A dining space with high chairs is visible in the background, enhancing the inviting atmosphere.

4.99 out of 5 average rating, 115 reviews

Private Home in The Berkshires (New Hot Tub!)

Leave your worries and stress behind and enjoy all the beautiful Berkshires have to offer! This fully remodeled home is ready to serve as your new favorite vacation spot! Whether you’re looking to enjoy a laid back getaway or an adventurous stay, look no further. You’re a short 10 minute drive to Ski Butternut, less than 15 minutes to Catamount, and about 20 minutes away from Tanglewood Music Center!

Popular amenities for Great Barrington house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.94 out of 5 average rating, 142 reviews

The spacious bedroom features a large bed with a geometric patterned duvet and plush pillows. Flanking the bed are two nightstands with lamps. A cozy area rug complements the hardwood floor. Robes are hung on the wall, and a doorway leads to the en suite bathroom.

Home in Saugerties

Bluestone Escape - Where everyone is at home.

4.96 out of 5 average rating, 173 reviews

A spacious cedar hot tub sits peacefully outdoors, surrounded by a natural setting of trees and open space. Bubbles rise from the water, creating a relaxing atmosphere. Clear blue skies are visible above, enhancing the tranquil environment.

Home in Hudson

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

4.89 out of 5 average rating, 181 reviews

A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.

Home in Rhinebeck

4Br Mountain Brook House on 130 acres w/ trails

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.

4.99 out of 5 average rating, 86 reviews

Stunning luxury home with fire pit

4.89 out of 5 average rating, 348 reviews

A tranquil swimming pond is framed by lush greenery and surrounded by wooden decking. Two lounge chairs are positioned on the deck, providing a relaxing spot to enjoy the natural scenery. A shaded area with wooden slats offers a cool retreat beside the water.

Home in Ghent

Modern Barn on 12 acres w Sauna, FirePit+swimming

4.92 out of 5 average rating, 101 reviews

Home in Hudson

Hudson River Sunset Getaway

5 out of 5 average rating, 110 reviews

A bright living area features large windows that invite natural light. The space includes a dark sofa, a vibrant yellow armchair, and a soft, patterned area rug. A coffee table is centrally placed, accompanied by a small side table with a decorative lamp.

Home in Taghkanic

Sunbeam Lodge: Sauna+Hot Tub, 50 Acres, ‘70s Oasis

Superhost

The exterior of the house showcases a combination of stone and brick, framed by well-kept landscaping. A mature tree offers shade in the front yard, while a pathway leads to the entrance. The roof features a peak with multiple gables.

Home in Kingston

4.79 out of 5 average rating, 116 reviews

Hudson River views with pool and hot tub

Weekly house rentals

4.86 out of 5 average rating, 36 reviews

A modern eat-in kitchen is highlighted by wooden beams and a rustic kitchen island. Wooden cabinetry complements the black appliances, while natural light pours in through sliding glass doors. A gray rug enhances the space, creating a functional and welcoming atmosphere.

Home in Sheffield

Cozy Cottage Route 7 Sheffield

4.93 out of 5 average rating, 80 reviews

A welcoming entryway features a vibrant yellow door framed by light fixtures, complemented by a decorative bear sculpture on a stone pathway. A large bush and windows add greenery to the red exterior of the house, creating a homey appearance.

Home in Copake

Yellow Door House

A spacious living area features high, vaulted ceilings and large windows that frame views of the outdoors. Two comfortable sofas are arranged around a central area rug, with a stone fireplace serving as a focal point. Shelving units display various decorative items, while a light floor lamp adds illumination.

4.93 out of 5 average rating, 30 reviews

Valley Vista atop Jug End

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.

5 out of 5 average rating, 28 reviews

Seekonk Hill

4.98 out of 5 average rating, 171 reviews

A serene landscape is captured, featuring a tall tree with budding leaves beside a rustic barn. Mist gently envelops the grassy area, creating a tranquil atmosphere as light filters through the trees in the background.

Home in Saugerties

The Stone House

4.94 out of 5 average rating, 150 reviews

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, 18 reviews

Lovely house in the Berkshires

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.

5 out of 5 average rating, 49 reviews

Sauna + Hot Tub Escape | Private & Pet Friendly

Private house rentals

An aerial view captures the tranquil lakeside retreat surrounded by lush greenery. The house is positioned near the water, offering easy access to the scenic lake, which is nestled within a rich landscape of trees and foliage.

4.97 out of 5 average rating, 69 reviews

Waterfront Modern Lake Mansfield Retreat

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.

4.96 out of 5 average rating, 55 reviews

River Cottage: Riverfront Home, Walkable Community

A spacious bedroom features a large bed adorned with white linens and decorative pillows. A warm fire crackles in a brick fireplace, complemented by wooden beams overhead. Soft lighting is provided by two bedside lamps, and a colorful area rug adds a touch of vibrancy to the room.

4.9 out of 5 average rating, 51 reviews

Cozy. Clean. Free bagel shop.

A newly renovated home is showcased amidst a wide expanse of lush green grass, surrounded by trees and open spaces. Bright blue skies feature soft, white clouds, creating a serene setting for relaxation.

5 out of 5 average rating, 26 reviews

Meadowbrook Cottage

A spacious Great Room features a pool table and a grand piano, with ample seating options including a leather sofa and armchairs. A rustic wooden coffee table sits atop a colorful area rug, creating a homey atmosphere next to a brick fireplace and large glass doors leading to the outdoors.

5 out of 5 average rating, 29 reviews

Berkshires Retreat!

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.

5 out of 5 average rating, 26 reviews

Berkshires Black Abbey - Ski Butternut

Superhost

5 out of 5 average rating, 6 reviews

A Berkshires Abode - Minutes to Ski & Downtown GB!

The modern kitchen features a stainless steel Viking stove, commercial-grade hood, and a farmhouse sink. White cabinetry and dark stone countertops create a stylish contrast. Natural light fills the space through large windows, accompanied by essential kitchen appliances arranged for easy access.