House vacation rentals in Great Barrington

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Top-rated house rentals in Great Barrington

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Guest favorite
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.
Home in Great Barrington
4.96 out of 5 average rating, 178 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.

Guest favorite
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.
Home in Great Barrington
4.94 out of 5 average rating, 124 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!

Top 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
4.94 out of 5 average rating, 144 reviews

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.

Guest favorite
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
4.95 out of 5 average rating, 105 reviews

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!

Top guest favorite
A charming two-story home is set on a landscaped plot with a gravel driveway. A wooden staircase leads to the entry, flanked by vibrant flower beds. The natural backdrop features lush trees and a striking granite ledge, creating a peaceful and inviting outdoor environment.
Home in Great Barrington
4.99 out of 5 average rating, 133 reviews

Granite Ledge, Modern home in a unique setting

Welcome to Great Barrington, the heartbeat of the Berkshires! This newly remodeled home that sits on 3.5 acres, is conveniently located 1 min from Butternutt Ski Mountain, and a 6 min drive from downtown main street Great Barrington. Convenient to restaurants, shops, farmers markets, art galleries, Tanglewood, Stockbridge, The Norman Rockwell Museum, Simon’s Rock, etc. Enjoy a vibrantly diverse restaurant scene and cultural events while still staying in a private setting.

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
4.99 out of 5 average rating, 117 reviews

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.

Top guest favorite
Home in Lee
4.99 out of 5 average rating, 295 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.

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
4.96 out of 5 average rating, 275 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 exterior of the house is showcased, featuring a red wood siding that complements the natural surroundings. Lush green grass and trees frame the property, while a hint of blooming foliage adds subtle color. The structure includes multiple sections with a sloped roof and chimney.
Home in Egremont
4.91 out of 5 average rating, 129 reviews

Beautiful Period Home in the Berkshires

Situated on 26 acres in the heart of the Berkshires in the small town of South Egremont, MA, this early 19th c. house combines the charm of the antique with all the modern conveniences including two screened-in porches. Conveniently located five minutes from Gt. Barrington, MA and 25 minutes from Stockbridge, Tanglewood, and Hudson, NY. The property also sits adjacent to the Appalachian Trail with plenty of local options for hiking and skiing.

Guest favorite
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, 288 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.

Guest favorite
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.
Home in Great Barrington
4.99 out of 5 average rating, 109 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!

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
4.98 out of 5 average rating, 124 reviews

Prime location for the best of the Berkshires

Our warm and welcoming little house has been designed and outfitted to be highly accommodating and comfortable. Our country living location is private but also super convenient: just a mile from Butternut Basin Ski Resort; walking distance to the Appalachian Trail; an easy 5 minute drive to Main Street Great Barrington; and shopping for staples is likewise close by.

Popular amenities for Great Barrington house rentals

Quick stats about house rentals in Great Barrington

  • Total rentals

    130 properties

  • Nightly prices starting at

    € 26 before taxes and fees

  • Total number of reviews

    4.5K reviews

  • Family-friendly rentals

    120 properties are a good fit for families

  • Pet-friendly rentals

    50 properties allow pets

  • Rentals with a pool

    10 properties have a pool

Destinations to explore