Vacation rentals with a patio in Great Barrington

Find and book unique accommodations with an outdoor patio on Airbnb

Top-rated accommodations with an outdoor patio in Great Barrington

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

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Guest favourite

Home in Becket

4.93 out of 5 average rating, 118 reviews

Lake front retreat - Stylish Berkshire home

Drive down a lovely country wooded road to this renovated 4 bedroom mid century home on Long Bow Lake. The house has wood floors throughout & hip design. Gas fireplace in the dining room. This will be a home for the family to enjoy. We have our own private lake frontage that includes a dock & 4 kayaks. Enjoy the screened in porch, Weber gas grill, ping pong table & games. The area is quiet & peaceful only 20 minutes from Downtown Lee, Outlets, fabulous hikes & minutes from skiing Otis Ridge.

Dec. 14 – 21

$542 CAD per night

Guest favourite

Guest suite in Great Barrington

5.0 out of 5 average rating, 45 reviews

Sweet 1-bedroom with salt water pool

Welcome to our home in the beautiful Berkshires! Enjoy this clean, private downstairs apartment with your own entrance. We are just 10-min from downtown Great Barrington and in a wonderful location for exploring. Upstairs is my family- a 6 year old boy and medium-sized dog- you will hear us! Sometimes we have friends and family visiting. In the summer you may see us at the pool with them. We’re happy to meet you and also happy to give you space- it’s your call. Wishing you a wonderful trip :-)

Sep. 30 – Oct. 7

$225 CAD per night

Guest favourite

Cabin in Tannersville

4.99 out of 5 average rating, 145 reviews

Cabin by the woods, Hunter Mountain & Kaaterskills

Our cozy little cottage is tucked away adjacent to the woods. This single floor 650sf apartment is a perfect place to unwind, build a bonfire, & enjoy the nature that surrounds you. Wake up in the morning to watch deer while enjoying your coffee on the porch. Main St. Tannersville is only an 8 min walk; with its nice selection of restaurants & shops. Hunter Mountain & Kaaterskill Falls are within a 10 min drive . Woodstock, Saugertise, Windham, Catskill & Kingston are within a 35 min drive.

Aug. 24 – 31

$222 CAD per night

Guest favourite

Apartment in Great Barrington

5.0 out of 5 average rating, 8 reviews

King Bed|2m Ski Resort|Stylish|Fast Wi-Fi

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 *9.9 miles to Tanglewood KEY FEATURES *MCM Design *Plush King Sized Bed high end bed Linens *High Speed Internet *Tv with Hulu Live+Roku

May 31 – Jun. 7

$243 CAD per night

Guest favourite

Cottage in Sheffield, The Berkshires

4.93 out of 5 average rating, 103 reviews

Cheerful 3-bedroom cottage with woodstove.

Relax with the whole family at this peaceful Berkshire getaway with easy access to all the area has to offer. A quick 20-minute drive to Butternut or Catamount ski hills, as well as downtown Great Barrington. Tanglewood and Jacob's Pillow are a half-hour's drive. Or stay at home and enjoy the peace and quiet of the surrounding woods, light a fire in the woodstove, cook in the large fully-equipped kitchen or head out back to barbecue on the large deck and play a game of badminton in the yard.

Nov. 15 – 22

$426 CAD per night

Guest favourite

Apartment in Hillsdale

4.96 out of 5 average rating, 74 reviews

Sweet Apt by Berkshires Catamount Walk to Brewery

Enjoy a stylish, elegant experience at this centrally-located newly restored 2 bedroom apartment with 1.5 baths in a historic building built in 1881, placed on the National Register of Historic places in 2010. Unit is on the 2nd floor and has a private entrance. Step back in time and stay in Second-Empire mansard Victorian that retains beautiful original details/layout and help it's restoration. Perfect location where the Hudson Valley meets the Berkshires. I have 4 other listings available.

Nov. 22 – 29

$177 CAD per night

Guest favourite

Home in Great Barrington

4.93 out of 5 average rating, 74 reviews

Best of the Berkshires + Hot Tub by Evergreen Home

Ski, hike, shop, and dine with this beautiful 2-bed, 1-bath Berkshires cottage as your home base. 15 minutes to the slopes or 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 available!

Nov. 11 – 18

$431 CAD per night

Guest favourite

Tiny homes in Catskill

4.93 out of 5 average rating, 132 reviews

Venster- Your window to wilderness

Two hours from NYC, close to skiing (hunter mountain/ Windham, Kaaterskill falls, Woodstock, Hudson, Saugerties. Book us and make Hudson Getaways your base station for all kinds of adventures. Enjoy facilities of a bigger house in a tiny form factor. Heat/AC, Queen bed, Hot shower, Kitchenette, cooktop, Fridge, Towels, linens, soap, coffee etc. *Hudson Getaways is a small woman owned business. We offer discounts to our social media followers, to returning guests and during slow seasons.

Aug. 6 – 13

$210 CAD per night

Guest favourite

Home in Great Barrington

4.97 out of 5 average rating, 38 reviews

Waterfront Modern Lake Mansfield Retreat

Stay directly on the water at this wonderful lakeside retreat. Please note: there will be construction on the road between the lake and the house, as well as the beach, starting Fall 2023 Enjoy views of the lake in the great room with fireplace, chefs kitchen and dining area, screened sunroom, 3 bedrooms and large upstairs loft. Central air, pickleball court, and EV charging. Walk to the best restaurants and shops in town. Steps to the public beach, as well as bike and hiking trails.

Jan. 4 – 11

$1,001 CAD per night

Guest favourite

Home in Great Barrington

5.0 out of 5 average rating, 67 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.

Nov. 27 – Dec. 4

$824 CAD per night

Guest favourite

Tiny homes in Chatham

4.99 out of 5 average rating, 147 reviews

BLUSH: Boutique TINY home*private spa*walk to town

Cozy in at this PRIVATE OASIS & just steps from quintessential Main St. Indulgences abound in this one-of-a-kind curated space w/ lounge in upstairs loft & PLUSH queen bed tucked in its own nook. Perfect for a couple or girlfriends getaway. Fully equipped kitchen. Enjoy the convenience of village life with restaurants, brewery, shops, theater. Hike, explore town, soak in your PRIVATE HOT TUB, make s'mores at the firepit, or tuck in & cozy. @artparkhomes

Aug. 6 – 13

$359 CAD per night

Guest favourite

Home in Great Barrington

5.0 out of 5 average rating, 8 reviews

Charming Cottage - Walk To Town

Keep it simple at this peaceful and centrally-located place. This cottage feels like a remote escape while still being walking distance to all of the shops and restaurants Great Barrington has to offer. Open concept main level with kitchen and cozy living room, upstairs has 2 bedrooms and the bathroom. Main bedroom has a queen bed while the second bedroom has a daybed with a trundle that can be made into one king size bed or two twin beds.

May 3 – 10

$504 CAD per night