House vacation rentals in Great Barrington

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Top-rated house rentals in Great Barrington

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

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Guest favorite
A spacious living room features a large U-shaped leather couch and a central ottoman, offering seating for several guests. Natural light pours through multiple windows, highlighting the wooden walls and stone accents. The kitchen area is visible in the background, enhancing the open layout.
Home in Great Barrington
4.85 out of 5 average rating, 124 reviews

Great Barrington, Cabin Sleeps 14, Walk To Town

You and your family cannot beat this PRIME location in downtown Great Barrington while still feeling remote and in the rolling hills of The Berkshires. Quick 20 minute drive to Tanglewood, 5 minutes to Ski Butternut, 15 minutes to Catamount Ski Mountain, 350 feet walking distance to all the great restaurants and shops of downtown Great Barrington and plenty more! Short walk to a great lake with a beach area - bring your dogs and family to swim in or walk around and enjoy the nature reservation!

Top 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, 126 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
4.95 out of 5 average rating, 149 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.

Top guest favorite
A spacious great room features a stone fireplace amidst large windows, allowing natural light to fill the space. A wooden dining table is placed near a comfortable sectional sofa, creating an inviting area for relaxation and dining. The warm wood beams add a rustic touch.
Home in Staatsburg
4.99 out of 5 average rating, 106 reviews

Boulder Tree House

Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

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, 293 reviews

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!

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, 120 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
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, 282 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.

Top guest favorite
A spacious living area features a large, cushioned sectional sofa in a warm hue, complemented by a round coffee table. Natural light floods through tall windows, highlighting a minimalistic bookshelf and a stylish armchair in the corner, enhancing the room's cozy atmosphere.
Home in Hudson
4.98 out of 5 average rating, 105 reviews

Chic Hudson Farmhouse w/ Fireplace & Porch

1873 Stylish & cozy Hudson Farmhouse w/ a wood burning stove & the perfect porch. 14 minute drive to Warren St This 3 bedroom + office home has been lovingly updated while maintaining the original details of this historic property. Located on over an acre of land, on a quiet street, this peaceful retreat is the perfect escape to unwind and relax. With high ceilings, tons of oversized windows, and an open layout, this house feels both airy & bright.

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
5 out of 5 average rating, 100 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.

Top 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, 112 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
An open kitchen and dining area feature rustic wooden beams and warm wooden floors. A round dining table with black chairs is positioned near double glass doors leading to a deck. An island with stools offers additional seating, with kitchen amenities visible in the background.
Home in Ghent
4.95 out of 5 average rating, 265 reviews

Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi

This charming location is perfect for a weekend (or longer!) getaway. With enough sleeping arrangements for 5 people, the cabin is ideal for a couple or a small group of close friends/family. Linens and toiletries are provided, as well as a fully stocked coffee bar. Escape from the everyday & enjoy experiences like Art Omi, local wineries, downtown Hudson & Chatham, skiing, hiking and so much more!

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, 125 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

When is the best time to visit Great Barrington?

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Quick stats about house rentals in Great Barrington

  • Total vacation rentals

    Explore 130 vacation rentals in Great Barrington

  • Nightly prices starting at

    Great Barrington vacation rentals start at € 26 per night before taxes and fees

  • Verified guest reviews

    Over 4,480 verified reviews to help you choose

  • Family-friendly vacation rentals

    120 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    130 of Great Barrington vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Great Barrington rentals

  • 4.9 Average rating

    Great Barrington stays are highly rated by guests—averaging 4.9 out of 5!

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