Vacation rentals with a patio in Berkshire County

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Top-rated patio rentals in Berkshire County

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Guest favorite

Barn in New Marlborough

4.93 out of 5 average rating, 40 reviews

Charming barn in the heart of the Berkshires

The rustic barn is in the center of Mill River, a charming, historic enclave in the Berkshires. Mill River is part of beautiful New Marlborough, MA. It has a wonderful general store, charming library, and Umpachene Falls for picnics and waterfall swimming! We are 15 minutes from Great Barrington and close to Tanglewood, The Mount, and Jacob’s Pillow. The barn is fully furnished with 1 king sized bedr, a pull out couch, and a modern open plan perfect for year-round stays (with central heating!).

Guest favorite

Home in Becket

4.93 out of 5 average rating, 136 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.

Guest favorite

Home in Lanesborough

4.95 out of 5 average rating, 40 reviews

Historic Stone Church in The Berkshires

<b>Hinterland Hall</b> was built in 1836 by the Saint Luke's Episcopal Parish and joined the National Register of Historic Places in 1972. Ripe with history and impeccable beauty, Ian & Jane purchased the old stone church in May of 2021, completing an extensive restoration process in accordance with the Massachusetts Historical Commission. It is with great pleasure that we open our doors to you for a wondrous stay. <b>Follow us @hinterlandhall</b> Please inquire about weddings & events.

Guest favorite

Rental unit in Otis

4.85 out of 5 average rating, 104 reviews

Fall Oasis in the Berkshires

Beautiful, centrally located home in Otis with seasonal water views of the reservoir! Just a few minutes drive from Otis ridge ski resort and the local lakeside beach for seasonal activities. This home is located next door to the only eat in Restaurant/Bar in town and even has a private trail that leads to this restaurant, Katies country store and boat Launch on the Otis reservoir! That same trail is also ride on snowmobile access for snowmobilers and enduro riders/mountain bikers and hikers.

Guest favorite

Cottage in Sheffield, The Berkshires

4.92 out of 5 average rating, 131 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.

Guest favorite

Place to stay in North Adams

4.93 out of 5 average rating, 137 reviews

Berkshire Mountain Top Chalet

Amazing mountain top lodge with beautiful views, and majestic log interior. Soaring ceilings, dramatic stone fireplace, and many more amazing amenities such as blazing fast internet, multiple decks, and hot tub. This gorgeous lodge is located near all The Berkshires has to offer—resplendent nature with waterfalls, hiking trails; cultural institutions such as Mass MoCA, and the Clark Institute; adventures such as zip-lining, white-water rafting, and skiing—it is the ultimate place for you.

Guest favorite

Home in Pittsfield

4.94 out of 5 average rating, 142 reviews

Cantabile life in the Berkshires

Relax with your family and friends after a day of skiing, hiking or a night of Tanglewood concert in this newly renovated home at the center of the Berkshires. Located in a quiet and friendly neighborhood, our home is 5min to Pontoosuc Lake and Lake Onota, 10min to Bousquet, 15min to Mt Greylock, 20min to Jiminy Peak and Tanglewood. Multiple grocery stores and shopping centers near by. Child/baby friendly, we have books, games, PingPong, foosball and a grand piano. Musicians are welcome!

Guest favorite

Guesthouse in Great Barrington

4.95 out of 5 average rating, 92 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.

Guest favorite

Home in Great Barrington

5 out of 5 average rating, 63 reviews

House in beautiful Berkshires

Welcome to our home in the beautiful Berkshires! Enjoy this clean, private upstairs of a split-level ranch house. We are just 10-min from downtown Great Barrington and in a wonderful location for exploring. We live downstairs- myself, a 7 year old boy and medium-sized dog. You may hear us :-) In the summer you may see us on occasion with friends and family in the saltwater pool. We’re happy to meet you and also happy to give you space- it’s your call. Wishing you a wonderful trip :)

Guest favorite

Home in Becket

5 out of 5 average rating, 39 reviews

Cozy lakehouse

Relax with family or friends at this sweet cottage on Center Lake in the Berkshires. This lakeside cottage is charming and rustic. Enjoy a beautiful day on the lake swimming, fishing off the dock and kayaking. Grill dinner on your private deck and watch the stars come out in the evening Or enjoy all that the Berkshires have to offer, Jacob’s Pillow (15 min), Berkshire Theater (20 min), Tanglewood (30 min). There are plenty of nearby hiking trails and charming towns to explore.

Guest favorite

Guesthouse in Stockbridge

4.88 out of 5 average rating, 17 reviews

Light-filled Carpenter's Cottage in Stockbridge

New to the market! This adorable wooden cottage feels bright, open, and spacious. It has modern amenities alongside its rustic charm. While it is a short distance away from our family home, there is ample privacy with a separate parking spot and walkway, landscaping, and a private deck. The cottage sleeps 2 in the queen sleigh bed, though there is ample room for a dinner party of 6. It sits on a south-facing hill, looking out towards Monument Mountain. We think you’ll love it!

Guest favorite

Home in Great Barrington

4.99 out of 5 average rating, 94 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.