Vacation rentals with outdoor seating in Great Barrington

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Top-rated outdoor seating rentals in Great Barrington

Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

An exterior view of the renovated red barn features a sloped roof and white-trimmed windows. Two white Adirondack chairs adorned with pink cushions are positioned on the grass, under the shade of a nearby tree, providing a cozy outdoor seating area.

Loft in Great Barrington

4.99 out of 5 average rating, 343 reviews

The Old Red Barn

Renovated studio in barn built circa 1830, centrally located to all activities in the Berkshires. Bright and sunny space with views of fields and spectacular sunsets. Open upstairs loft bedroom with pine floors, catherial ceiling, exposed beams, full kitchen , bathroom and washer and dryer. The Berkshires are beautiful in the fall , come stay ! 5 minute drive to town. Walk to the Green River , hike the trails. We provide all basic household supplies. We invite all to enjoy our old red barn.

Guest favorite

A charming architectural structure is nestled among lush greenery, framed by a variety of trees. A rustic wooden bench sits in the foreground, inviting guests to relax and enjoy the serene natural surroundings. Soft light emanates from the windows, enhancing the inviting atmosphere.

Chalet in Otis

4.95 out of 5 average rating, 436 reviews

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Guest favorite

Apartment in Philmont

4.9 out of 5 average rating, 129 reviews

Beautiful space in the heart of Philmont

Enjoy the elegant ambience of this airy and bespoke space, just two doors up from the excellent restaurant Local 111, as well as the Co-op, where you can pick up delicious local produce, meats, and baked goods. A couple blocks from the Philmont Pub, another fantastic place to eat and enjoy the evenings. Minutes from Hudson, this town is literally in the center of Columbia County. A short drive to Catamount, Bash Bish, the Hudson River, the Catskills, the Berkshires, no end of places to explore!

Guest favorite

A living area is visible, featuring a sleek gray couch and a modern chair positioned near a stylish fireplace. Artwork is displayed on the wall, and natural light illuminates the space. A neutral rug adds texture to the polished floor, with a bedroom area partially seen in the background.

Apartment in Copake Falls

4.91 out of 5 average rating, 347 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

Guest favorite

A detached red barn is surrounded by a grassy yard, with patches of snow visible on the ground. The property features a gravel driveway leading to the barn's double garage doors. Mature trees line the background, offering a natural setting.

Guesthouse in Lenox

4.9 out of 5 average rating, 273 reviews

The Coach House | Modern 2BR Loft + Views & Pool

Restored coach barn with 25-ft cedar ceilings, skylights, and mountain views—part of House on Golden Hill, a historic Lenox farmhouse compound. This airy 2BR + loft retreat blends rustic charm with modern ease. Enjoy a full kitchen, cozy living space, and outdoor area. Set beside a stream with seasonal pool access, it’s perfect for families, couples, or creative escapes. Centrally located and just minutes to downtown Lenox, Tanglewood, and trails—your Berkshires base for rest and inspiration.

Guest favorite

A modern bedroom features a plush King-sized bed with crisp white linens and decorative pillows. A door opens to an outdoor area, while a unique wall design adds architectural interest. A small console table with a coffee maker is positioned against the wall.

Apartment in Great Barrington

4.95 out of 5 average rating, 101 reviews

King Bed, Wi-Fi, 2m Ski Resort

Remodeled Mid-Century Motel, that sits in the heart of the Berkshires. Located in Great Barrington, MA. Just steps from fantastic restaurants, eateries, shops, etc. A very short drive to Butternut Ski Resort. * 1.5 miles to Downtown * 1.3 miles to Mahaiwe Performing Arts Center * 44 miles to Albany International Airport *4.5 miles to Great Barrington Airport KEY FEATURES: *MCM Design * Plush King Sized Bed w/ high end Centium Satin Linens *High Speed Internet *55" Youtube TV with NFL Pack

Guest favorite

A charming cottage is framed by vibrant flowering shrubs and greenery. The front porch is adorned with decorative elements, while large windows invite natural light into the space. A wooden fence encloses the front garden, enhancing the quaint and inviting atmosphere.

Cottage in Great Barrington

4.93 out of 5 average rating, 308 reviews

Artist Cottage

Enchanting, private, romantic, retro style, artsy, cottage & lodge building with fireplaces and outdoor hot tub and shower area in a quaint, quiet, neighborhood nested at the base of Flag Rock and near nature trails and downtown Great Barrington. Perfect for a romantic get-away. Open retro style kitchen with wood stove and TV is stocked with utensils and pans for cooking with gas oven and retro appliances. Upstairs bedroom with ensuite large bathroom with soaking tub and message chair.

Top guest favorite

A spacious living area features comfortable seating, a glass coffee table, and a dining space with wooden chairs. The kitchen is visible, showcasing modern appliances and a light wood countertop. Natural light illuminates the room, creating a warm and open atmosphere.

Apartment in Sheffield

5 out of 5 average rating, 378 reviews

Hideaway with Spectacular Berkshire Views

Located on the border of Massachusetts and Connecticut with spectacular views of the Berkshire Hills and fifteen minutes drive from Great Barrington, MA, this apartment is located on a secluded seven-acre property. Owners live on the property. Above an artist studio this renovated one bedroom apartment with private entrance, full kitchen, fast internet is stylish, light and airy with a contemporary and eclectic decor. Please note During winter all-wheel drive vehicle is strongly advised.

Top guest favorite

A charming two-story house is set against a vibrant sunset sky, with mountains and trees in the background. A covered porch extends across the front, providing a welcoming entrance, while a trampoline is placed on the spacious lawn.

Guest suite in Great Barrington

4.98 out of 5 average rating, 122 reviews

Hillside Haven

Ideally located on “the hill” in a beautiful and quiet neighborhood just a short walk to downtown Great Barrington’s amazing cafes, restaurants, ice cream, and Lake Mansfield’s beach and loop trail. The perfect hillside haven for those looking to be in the center of it all. This private, modern, and clean space is completely new as of mid-2021 and has a well-appointed kitchen, outdoor patio with a firepit, fast internet, covered parking, radiant heat floors, and an air conditioning unit.

Guest favorite

An open, airy space features a wooden staircase leading to the upper level. A small dining area includes a table and two stools, while a comfortable seating area is visible in the background. Natural light filters through large windows, illuminating the modern design.

Vacation home in Great Barrington

4.94 out of 5 average rating, 239 reviews

Home in Great Barrington. Steps from downtown!

First Things First… Let’s Keep the Love Alive! ❤️ 🙌 Central and Private! Just steps away from historic downtown Great Barrington. East Mountain Hiking trails are a quick walk away. Enjoy sunset views with friends and family, before you walk into town for a night out! Butternut Ski Area: 5-10 min drive(traffic depending) Tanglewood: 20-25 min This new home features all new appliances and furniture. Enjoy luxury, charm, and privacy while you rest easy at The Maple. 🫶

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, 130 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, 114 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.