Vacation rentals with a patio in West Stockbridge

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Top-rated patio rentals in West Stockbridge

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Guest favorite

Home in West Stockbridge

5.0 out of 5 average rating, 54 reviews

Heart of the Berkshires - Bright, Cozy, Near Lake

Welcome to the heart of the Berkshires! This newly furnished home is conveniently located between downtown Stockbridge and Lenox. Minutes to Tanglewood, the Stockbridge Bowl, restaurants, shops, art galleries, Canyon Ranch, Berkshire Botanical Gardens, the Norman Rockwell Museum, etc. A short drive to four ski resorts, including Butternut, Catamount, Bousquet, and Jiminy Peak. Enjoy a diverse culture and restaurant scene and everything that the Berkshires has to offer. Fast wi-fi is available.

May 31 – Jun 7

G$130,955 GYD 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.

Nov 22 – 29

G$78,842 GYD 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 9 – 16

G$30,912 GYD per night

Guest favorite

Home in West Stockbridge

5.0 out of 5 average rating, 29 reviews

Berkshires Forest Retreat with Hot Tub

A freshly renovated modern home, set on 3.5 private acres at the end of a cul-de-sac is the perfect home base for your Berkshires getaway. Drive 6 minutes to Tanglewood & be in downtown Lenox in less than 10 minutes! Located in picturesque Stockbridge, MA this home is a short drive from Tanglewood, Wineries, Museums, Theatre, Skiing, Hiking, Golf, Shopping and Dining. Enjoy quiet country living, minutes from all Berkshires attractions. Longer stays are welcome. Ask us about monthly discounts!

May 9 – 16

G$83,500 GYD 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.

Oct 26 – Nov 2

G$26,738 GYD 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

Mar 8 – 15

G$22,616 GYD per night

Guest favorite

Tiny home in Catskill

4.93 out of 5 average rating, 135 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

G$30,343 GYD per night

Guest favorite

Cabin in West Stockbridge

4.98 out of 5 average rating, 48 reviews

Modern Cabin near Tanglewood

Welcome to West Stockbridge in the Berkshires! This newly renovated modern cabin is nestled amongst the trees and located just 3 miles from the famous Tanglewood and Kripalu. Right down the street is main street where you can peruse the shops, grab a gourmet coffee, or listen to more music at the Foundry. There are restaurants, hiking trails, waterfalls and lakes less than a mile away. We are 5 minutes from the turn pike for easy directions! Come hang and enjoy all the activity and beauty.

Dec 8 – 15

G$89,286 GYD 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.

Jun 1 – 8

G$38,378 GYD per night

Guest favorite

Home in Canaan

4.96 out of 5 average rating, 27 reviews

Crossings Cottage

Welcome to Crossings Cottage! Conveniently located in the heart of the bucolic Berkshires right on the Massachusetts, New York State line. This beautiful property sits tucked down a country road just 1 mile from the Mass Pike and New York State Thruway, making it very easy to access. The Cottage sits on 50+ acres with panoramic views of the property off the back deck. Its location is only 8 miles from Tanglewood, Lenox, and Stockbridge! Home Range Winery is only a 5 minute walk!

Jan 19 – 26

G$66,988 GYD per night

Guest favorite

Home in West Stockbridge

5.0 out of 5 average rating, 16 reviews

Beautiful And Private Home Centrally Located

This beautiful and private home is centrally located at 14 Glendale Road in West Stockbridge (Housatonic), MA. The location has access to all of the Berkshires great attractions. 5 minutes to Norman Rockwell Museum, 10 minutes to Tangelwood, 15 minutes to Butternut Ski Area, 20 minutes to Catamount Mountain Resort, and minutes to fantastic restaurants, hiking/biking trails, and arts/culture. There are also 4 acres of groomed private hiking trails on the property.

Nov 6 – 13

G$198,508 GYD 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 23 – 30

G$29,018 GYD per night