Vacation rentals with a patio in Great Barrington

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Top-rated patio rentals in Great Barrington

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Guest favorite

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 9 – 16

R6,541 ZAR per night

Guest favorite

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 10 – 17

R2,704 ZAR per night

Guest favorite

Apartment in Great Barrington

5.0 out of 5 average rating, 12 reviews

King Bed|Wi-Fi|2m Ski Resort|Studio|Berkshires

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

Jun 1 – 8

R2,906 ZAR per night

Guest favorite

Cottage in Sheffield, The Berkshires

4.93 out of 5 average rating, 104 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.

Jan 2 – 9

R4,278 ZAR per night

Guest favorite

Apartment in Hillsdale

4.96 out of 5 average rating, 75 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.

May 31 – Jun 7

R2,424 ZAR per night

Guest favorite

Home in Great Barrington

4.93 out of 5 average rating, 75 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!

Jun 9 – 16

R4,905 ZAR per night

Guest favorite

Tiny home in Catskill

4.93 out of 5 average rating, 133 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.

Feb 3 – 10

R2,754 ZAR per night

Guest favorite

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.

Feb 20 – 27

R11,385 ZAR per night

Guest favorite

Guesthouse in Great Barrington

4.96 out of 5 average rating, 50 reviews

Sweet Victorian in Housatonic

Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newly renovated Victorian house in Housatonic. Tasteful clean furniture, organic new sheets, pillows and duvets. Lovely clean kitchen that is fully equipped to host dinners. Situated up on a hill in Housatonic this three bedroom is conveniently located to to Great Barrington, Lake Mansfield, Stockbridge, Butternut, Catamount, Tanglewood, Kripalu and Monument Mountain.

May 26 – Jun 2

R2,913 ZAR per night

Guest favorite

Home in Hillsdale

5.0 out of 5 average rating, 23 reviews

Enjoy all 4 Seasons

Newly renovated, a mix of country and modern furnishings. Bright, sunny and airy feel. Located on 1 acre with a beautiful sun-soaked deck. Easy access to Hillsdale, Rail Trails, 20 minutes to Hudson, Great Barrington, Catamount Ski & Adventure Park. Sleeps 6 comfortably, 2-bdr, 1 large bath, spacious living and dining. Kitchen with lots of natural light and deck access. Relax on hammock, swing in a tire, or sit by the fire. Washer and dryer available for use.

Jan 18 – 25

R2,636 ZAR per night

Guest favorite

Tiny home in Chatham

4.99 out of 5 average rating, 151 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

Jul 8 – 15

R4,718 ZAR per night

Guest favorite

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 10 – 17

R5,754 ZAR per night