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Vacation rentals with outdoor seating in Berkshire County

Find and book unique outdoor seating rentals on Airbnb

Top-rated outdoor seating rentals in Berkshire County

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

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Cabin in Stephentown

4.86 out of 5 average rating, 267 reviews

Cabin in the woods w cedar Hot Tub + private pond

The Hemlock Hideaway is a charming, rustic cabin in the woods designed for rest and relaxation. Guests will journey into simpler times, inspired by antique furnishings that remind them to slow down and unwind during their stay. The cabin is isolated yet only 10 min drive to Jiminy Peak for skiing as well as park and trails for hiking, apple orchards, excellent restaurants and foliage viewings. Cherry Plain State Park, Mount Greylock, Lebanon Speedway, Albany, and Pittsfield are all 25 min max.

Loft in Great Barrington

4.99 out of 5 average rating, 317 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.

Chalet in Otis

4.95 out of 5 average rating, 382 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

Home in Lee

4.9 out of 5 average rating, 253 reviews

Cozy Berkshires Cottage

Stay in a cozy Berkshires 1920's cottage! The bedroom occupies the entire second floor with peaceful views of the surrounding field and yard. The cottage is set back from the main road, easily accessible yet private. - Zoned air conditioning & heating makes every room comfortable year-round. - Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. - Ideal for couples, solo adventurers, business travelers, and furry friends (pets). (Note: MA requires 11.7% tax added to charges)

Rental unit in Copake Falls

4.92 out of 5 average rating, 300 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!

Cottage in Great Barrington

4.93 out of 5 average rating, 266 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.

Rental unit in Canaan

4.99 out of 5 average rating, 147 reviews

Mountain View Getaway

Come relax & enjoy panoramic mountain and pond views. Marvel at the dramatic lighting effects on Mercer Mt from sunrise-sunset from your private deck or bright living room. Fully equipped kitchen, grill on the deck, short scenic drive to a wide variety of restaurants & endless cultural venues in the surrounding quaint villages of Berkshire County Mass and Columbia County NY. Near hiking trails, skiing, apple picking & farm stores. Queechy Lake swimming, NYS boat launch for car top boats.

Home in Becket

4.87 out of 5 average rating, 323 reviews

Real Estate:Therapy - Lake, Laundry, Love it

This is what happens when a realtor and an expressive-therapist make a vacation home. You get a decent property, in a good location with little things to help you de-stress, have fun and connect with friends and family. 18 minutes from downtown Lee, in the private Sherwood Forest Community with lake access, laundry, and a level-2 EV charger, this 1500 sq. ft home built in 1987 rejuvenates. We hope you will leave here a little more relaxed, recharged or maybe even a little bit happier.

Farm stay in Pittsfield

4.99 out of 5 average rating, 171 reviews

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.

Guesthouse in Lenox

4.94 out of 5 average rating, 341 reviews

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.

Cottage in Lanesborough

4.93 out of 5 average rating, 143 reviews

The Sail Loft

Cozy, private house from 1850, located in the heart of the Berkshires. On a quiet street across from a pond, the cottage has access to the Ashuwillticook rail trail. Relax on the private back porch, or in the large bath tub. Sleep in late in the king sized bed, and then enjoy what the Berkshires has to offer. Close to several downhill and cross country ski spots, hiking trails and Tanglewood!

Vacation home in Great Barrington

4.95 out of 5 average rating, 189 reviews

Home in Great Barrington. Steps from downtown!

Central and Private! Just steps away from historic downtown Great Barrington and East Mountain Hiking trails. Enjoy sunset views with friends and family, before you walk into town for a night out! 10 minutes (2 miles) to Butternut Ski Area This brand new home features all new appliances and furniture. Enjoy luxury, charm, and privacy while you rest easy at The Maple.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Chalets

Adventure-ready homes with après-ski style

Popular amenities for Berkshire County outdoor seating rentals

Free parking on premises

Air conditioning

House rentals with outdoor seating

Home in Williamstown

4.98 out of 5 average rating, 125 reviews

Quality, Comfort, Charm in Williamstown Center

Home in Stockbridge

4.97 out of 5 average rating, 104 reviews

Greek Revival Farmhouse

Home in Monterey

4.92 out of 5 average rating, 130 reviews

Perfect Berkshire getaway.Cozy cottage.Great wifi.

Home in Egremont

4.98 out of 5 average rating, 125 reviews

A sunny, quiet chalet beautifully decorated.

Home in Stockbridge

4.95 out of 5 average rating, 120 reviews

Sun-filled, Charming Stockbridge Classic- In Town!

Home in Pittsfield

4.94 out of 5 average rating, 144 reviews

Cantabile life in the Berkshires

Home in Cheshire

4.86 out of 5 average rating, 211 reviews

19th c. Barn in The Berkshires

Home in Dalton

4.93 out of 5 average rating, 184 reviews

Brooksong, the perfect Berkshires getaway

Apartment rentals with outdoor seating

Rental unit in Great Barrington

5 out of 5 average rating, 111 reviews

Walk Everywhere! | Relax in Easy Elegance!

Rental unit in Sheffield

4.92 out of 5 average rating, 139 reviews

Private Berkshire Barn Apartment

Rental unit in North Adams

4.98 out of 5 average rating, 190 reviews

Overlooking the city in a quiet 7 unit building.

Rental unit in East Chatham

4.95 out of 5 average rating, 109 reviews

Bennett Abode

Rental unit in Petersburg

4.87 out of 5 average rating, 171 reviews

The Beer Diviner Brewery Apartment

Rental unit in Williamstown

4.93 out of 5 average rating, 282 reviews

COLD SPRING

Rental unit in North Adams

4.97 out of 5 average rating, 490 reviews

Steps to MoCA, near SKI: 2bd + SAUNA!

Rental unit in Sheffield

5 out of 5 average rating, 344 reviews

Hideaway with Spectacular Berkshire Views

Condo rentals with outdoor seating

Condo in Hancock

4.98 out of 5 average rating, 42 reviews

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

Condo in Hancock

4.85 out of 5 average rating, 142 reviews

Cozy Condo @ Jiminy Peak

Condo in Lenox

5 out of 5 average rating, 30 reviews

Spacious 3 bedroom apt in Lenox historic downtown

Private room in Great Barrington

4.94 out of 5 average rating, 176 reviews

Quiet refuge in Great Barrington

Condo in Hancock

4.88 out of 5 average rating, 32 reviews

All-season Berkshires ski resort condo - Sitzmark

Destinations to explore