Vacation rentals with outdoor seating in Great Barrington

Find and book unique accommodations with outdoor seating on Airbnb

Top-rated accommodations with outdoor seating in Great Barrington

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

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Guest favourite

Loft in Great Barrington

4.99 out of 5 average rating, 296 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.

May 23 – 30

$263 CAD per night

Guest favourite

Home in Lee

4.89 out of 5 average rating, 235 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)

Oct. 7 – 14

$211 CAD per night

Guest favourite

Apartment in Copake Falls

4.93 out of 5 average rating, 258 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!

Sep. 13 – 20

$216 CAD per night

Guest favourite

Tiny homes in Chatham

4.99 out of 5 average rating, 183 reviews

Tiny House on 70 Private Acres in Hudson Valley

Welcome to "The Tiny" at The Hemptons in Upstate New York! The not-so-tiny house is 400sf with plenty of space to stretch out. Each of the two bedroom lofts have a comfy queen bed on a low profile frame. The kitchen is equipped for basic cooking (read: Not good for Thanksgiving, but perfectly suited for standard cooking endeavors). Although we'd encourage you to check out many the local eateries (see below)! The bathroom is full size and likely bigger than the one in your first NYC apartment.

Jun. 3 – 10

$224 CAD per night

Guest favourite

Apartment in Sheffield

5.0 out of 5 average rating, 319 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.

Dec. 13 – 20

$266 CAD per night

Guest favourite

Guest suite in South Lee

4.92 out of 5 average rating, 190 reviews

Sunny Riverside Apartment

The Berkshires are a perfect spot for a getaway week or weekend. You will enjoy this cozy 2-story apartment, easily accessible to all that the region has to offer. The apartment has a fully equipped kitchen, dining space, living area, and two bedrooms, overlooking the Housatonic River. Every town in South County is 5-15 minutes drive, and in 50 minutes you could be at The Clark Museum or Mass MOCA in North County. Several ski areas are nearby, and Kripalu is just an easy 10 minute drive.

Mar. 22 – 29

$196 CAD per night

Guest favourite

Cottage in Hillsdale

4.94 out of 5 average rating, 171 reviews

Cozy Cottage Catamount, Berkshires Walk to Brewery

This cute, cozy cottage is located in the center of Hillsdale, NY on the grounds of the Second Empire landmark Mount Washington House, located in the hamlet’s National Historic District. The cottage is perfectly located between Hudson, NY and Great Barrington, MA and you can walk to stores, parks, Roe Jan Brewing Company, Taconic Ridge, the Harlem Valley Rail Trail and more. Very close to Catamount Mountain Resort, Copake Lake and Bash Bish Falls. Public EV charger located in west lot.

May 29 – Jun. 5

$181 CAD per night

Guest favourite

Guesthouse in New Marlborough

4.91 out of 5 average rating, 179 reviews

COZY GUESTHOUSE MINUTES AWAY FROM HIKING!

Renovated 1880's one bedroom cozy guesthouse in beautiful Southfield, MA. Full kitchen stocked with all necessities. Comfortable & stylish with a luxury king size bed. Minutes away from Ski Butternut, Berkshire attractions & trails. Walking distance to breakfast and lunch at The Southfield Store or have dinner at nearby The Old Inn On The Green and Cantina 229. 10 minutes from Great Barrington. Enjoy leaf-peeping, hiking, waterfalls, apple picking, skiing, and much more!

Jul. 29 – Aug. 5

$265 CAD per night

Guest favourite

Guesthouse in Lenox

4.95 out of 5 average rating, 281 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.

Sep. 4 – 11

$226 CAD per night

Guest favourite

Farm stay in Pittsfield

4.99 out of 5 average rating, 105 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 take a walk on our hiking trail.

Sep. 7 – 14

$184 CAD per night

Guest favourite

Barn in Hillsdale

4.97 out of 5 average rating, 117 reviews

Hudson Valley Hilltop Barn

A private hilltop oasis in nature. Newly renovated barn with some luxury amenities including sauna & outdoor firepit & movie theater screen & on a 15-acre hilltop with views & privacy in Hudson Valley / Berkshires. Fully stocked for cooking and tons of games. Perfect for winter sledding right on our hill. 100 acres of untouched nature around property. Near great shops & restaurants in Hudson & Great Barrington. *Pets must get written approval*

Sep. 23 – 30

$1,552 CAD per night

Guest favourite

Apartment in Sheffield

4.92 out of 5 average rating, 122 reviews

Private Berkshire Barn Apartment

A private entrance and apartment all to yourself. You are within a 2 minute drive of downtown Sheffield or a 10-15 minute walk. Also within a short drive of superb restaurants and local ski areas, Great Barrington, Tanglewood, Jacobs Pillow, The Rockwell Museum and numerous other Berkshire attractions. Also within a short drive of Berkshire, Salisbury, Hotchkiss and Simon's Rock schools.

Dec. 5 – 12

$227 CAD per night