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

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

ﺩ.ﺇ1,267 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 30 – Oct 7

ﺩ.ﺇ484 per night

Guest favorite

Home in Otis

4.83 out of 5 average rating, 59 reviews

Springtime 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.

Jun 19 – 26

ﺩ.ﺇ431 per night

Guest favorite

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

ﺩ.ﺇ947 per night

Guest favorite

Apartment in Great Barrington

5.0 out of 5 average rating, 15 reviews

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

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 *58"Tv with Hulu Live

Mar 9 – 16

ﺩ.ﺇ627 per night

Guest favorite

Place to stay in North Adams

4.93 out of 5 average rating, 114 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.

Dec 23 – 30

ﺩ.ﺇ2,056 per night

Guest favorite

Home in Cheshire

5.0 out of 5 average rating, 22 reviews

The Berkshires Hummingbird House

Enjoy beautiful lake view sunsets from the comforts of your living room. This bright and airy 3 bedroom home sits on an acre overlooking Cheshire Lake and is mere steps to the Ashuwillticook Rail Trail bike path. Centrally located in the Berkshires, this convenience allows for short drives to hikes at Mt Greylock Reservation, arts venues MASS MoCA, the Clark and Tanglewood, numerous ski areas, shopping/dining options, and countless other outdoor activities and cultural attractions.

Nov 15 – 22

ﺩ.ﺇ782 per night

Guest favorite

Home in Adams

4.91 out of 5 average rating, 68 reviews

Mountain View Hideaway

Welcome to the Hideaway! This 800sqft home is located on a small hill with a beautiful direct view of Mount Greylock. This amazing home is perfect for anyone who's looking to explore the Berkshires by day and come back to a tranquil home by evening. This small but mighty house has a full kitchen, very comfortable lounging couch, quiet bedroom with an adjacent office area, full bathroom with a washer and dryer and a front and back yard. Everyone is welcomed to enjoy this gem of a home!

Sep 6 – 13

ﺩ.ﺇ466 per night

Superhost

Apartment in Pittsfield

4.86 out of 5 average rating, 42 reviews

The Sunset Sanctuary - King Bed with Kitchen

Welcome to our cozy 1-bedroom apartment with a charming front porch and a private entrance with ample parking! Nestled in a peaceful neighborhood, this inviting retreat is the perfect place for a relaxing getaway or a romantic escape. The house is located just opposite of the Cumberland gas station where you can get breakfast, snacks, drinks or coffee along with any essentials. It’s only 3 mins drive from the Berkshire Medical Center and 20 mins drive from Tanglewood.

Mar 26 – Apr 2

ﺩ.ﺇ247 per night

Guest favorite

Apartment in Otis

4.98 out of 5 average rating, 60 reviews

Enjoy every season the Berkshires have to offer.

Come enjoy the Berkshires any season you choose. We are close to local ski areas, with have access to snow shoeing, ice fishing and many more winter activities. Also located within minutes of the many cultural attractions the Berkshires have to offer, Jacob's Pillow, Shakespeare & Company, and Tanglewood. Enjoy the beautiful fall foliage on our small private pond. You can bring your kayak or canoe to enjoy the wildlife that abounds or catch & release in our pond.

Aug 22 – 29

ﺩ.ﺇ632 per night

Guest favorite

Apartment in Adams

4.88 out of 5 average rating, 58 reviews

Mountain Living, 1-bedroom unit, outdoor hot-tub

Relax & enjoy nature in this tranquil, 1 bedroom unit down the block from Mt. Greylock, highest mountain in MA! 2 minutes away from hiking trails, 10 minutes away from Mass Moca, 25 minutes away from Jiminy Peak ski resort. Enjoy MT Views, and jump in the outdoor jacuzzi right outside your bedroom. WiFi, AC, your own thermostat & TV. The suite you’ll be staying in is directly attached but separate access from the main house. Military and HCP discounts

Aug 5 – 12

ﺩ.ﺇ340 per night

Guest favorite

Vacation home in Great Barrington

4.94 out of 5 average rating, 140 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.

Apr 5 – 12

ﺩ.ﺇ1,041 per night