Vacation rentals with a patio in Sheffield

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Top-rated patio rentals in Sheffield

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Guest favorite

Apartment in Great Barrington

5.0 out of 5 average rating, 8 reviews

Berkshire Retreat|King Bed|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 and 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

May 14 – 21

ﺩ.ﺇ472 per night

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.

May 7 – 14

ﺩ.ﺇ1,221 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 :-)

Oct 21 – 28

ﺩ.ﺇ494 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.

Jan 9 – 16

ﺩ.ﺇ846 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.

Sep 11 – 18

ﺩ.ﺇ480 per night

Guest favorite

Home in Copake

4.92 out of 5 average rating, 39 reviews

Yellow Door House

Stay at our casual, pet friendly property in the beautiful Hudson Valley. Vaulted ceiling great room opens into the kitchen & sunroom, with 2 cozy bedrooms rounding out the space. The yard is extensive with a deck & fire pit, backing up to a wooded area. Nearby Robinson Pond offers swimming & kayaking. While dogs aren’t allowed on the beach, they will love the quiet walkable roads. Hudson NY, Great Barrington MA, Bash Bish Falls, Harlem Valley Rail Trail & Catamount are all within 30 minutes

Aug 6 – 13

ﺩ.ﺇ534 per night

Guest favorite

Cabin in Canaan

4.96 out of 5 average rating, 67 reviews

Dog Friendly Log Cabin of Your Dreams!

Sage Cabin sits at the mouth of the Berkshires, at the intersection of Connecticut, Massachusetts, and New York State. A 5-15 minute drive in any direction will bring you to amazing food & drink, antiquing, and hiking. Have dogs? Get their zoomies out in the fenced backyard. Working from home? There's a work station & fast wifi all set up for you. Love winter sports? Butternut & Mohawk Mountain for skiing/snowboarding are minutes away. Or, grab the snowshoes in the basement & hike around!

Sep 28 – Oct 5

ﺩ.ﺇ1,017 per night

Guest favorite

Tiny home 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

ﺩ.ﺇ545 per night

Guest favorite

Home in Sheffield

5.0 out of 5 average rating, 11 reviews

Charming Country House with a Hot Tub

Nested in the southern Berkshire County, this private house is perfect for all seasons. It's a 15 minute drive from Great Barrington as well as skiing, swimming lakes, trails and tons of nature. Set on a secluded 2-acre lot, the house offers ample outdoor space with a hot tub that runs all year, a firepit and out door dining area. The house features an open kitchen and dining area, a spacious and well-appointed living room with a gas fireplace, kids play area, a garage with EV charging.

Apr 14 – 21

ﺩ.ﺇ1,868 per night

Guest favorite

Home in Sheffield

5.0 out of 5 average rating, 26 reviews

The Kellogg House in the Heart of The Berkshires

The Kellogg House is conveniently nested in the heart of the Berkshires. Located within a short car ride from Sheffield, Great Barrington, and South Egremont, the area offers a superb food scene, local shopping, and cultural experiences. Cross Kellogg Rd, and you will find yourself on the 2,200 mile long Appalachian Trail. From lakes to mountains, you can access all that the Berkshire has to offer within minutes. The house is ideal for singles, couples, and families with children.

Dec 15 – 22

ﺩ.ﺇ892 per night

Guest favorite

Cabin in Pine Plains

4.98 out of 5 average rating, 175 reviews

The Upstate A - Modern Luxury in the Hudson Valley

The Upstate A is a 3 bedroom + sleeping loft, 2.5 bathroom A-frame set on a quiet cul-de-sac in the heart of the Hudson Valley. Built in 1968, it was fully renovated in 2020-2021. Staying here you’ll experience a cozy yet modern vibe, immersed in nature but with all the accoutrements of an upscale stay. You'll find great hiking in the summer, skiing in the winter, fresh upstate air year-round and serenity all day and night. See for yourself: check us out on IG @upstate_aframe

Nov 15 – 22

ﺩ.ﺇ2,365 per night

Guest favorite

Home in Sheffield

4.98 out of 5 average rating, 45 reviews

Walt's Place-Your Family Getaway

Relax with the whole family at our beautiful, quiet, and contemporary family retreat. Walt's Place offers elevated furnishings and finishes and is nestled in the woods near Salisbury, CT, and Great Barrington, MA. Whether you’re here alone or with your family, for vacation or a work getaway, you’ll find everything you need in this comfortable home. The location is ideal: close to nearby towns and some of the best outdoor activities in the Berkshires.

Sep 24 – Oct 1

ﺩ.ﺇ1,617 per night