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Vacation rentals with a patio in West Stockbridge

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Top-rated patio rentals in West Stockbridge

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Top guest favorite

The living area features vaulted wood-paneled ceilings and large windows, allowing natural light to fill the space. A cozy seating arrangement includes a sofa and a table. A pellet stove is situated for warmth, while sheer curtains provide a soft filtering of light.

Cabin in Saugerties

4.99 out of 5 average rating, 143 reviews

Sweet Saugerties A-Frame - 10 mins from Woodstock

This sweet A-Frame hideaway located in a wooded area between Saugerties and Woodstock will welcome you and warm your spirit with its charm. Featuring 2 bedrooms, each with Queen Beds, and a couch that folds out to a Full Bed, there's ample space for 4. But, it's also a serene escape for an individual or couple. An inspiring creative retreat, the home has beautiful views, and an electric piano. Quiet but 10 mins from great restaurants! 11 mins to HITS, 30 mins to skiing at Hunter Mountain.

Top guest favorite

A cozy sleeping area is highlighted by a spacious bed dressed in neutral linens. An inviting cushion rests on the bed, while warm light emanates from two bedside lamps. A wooden bench sits at the foot of the bed, and decorative greenery adorns the walls.

Guesthouse in Cummington

5 out of 5 average rating, 129 reviews

Cozy Hilltown Cottage

Enjoy a peaceful stay in this cozy, creative space. Set on 10 acres of gardens and woods, this cottage is perfectly located to explore Western Massachusetts - with places like MASS MoCA, Shelburne Falls, Tanglewood and Northampton all within a 30min to 1 hour drive. Upstairs is a queen bed and full bath, while downstairs features a functional kitchen, work desk, grand windows, and a living space with full sleeper sofa. We live in the main house on property but respect your privacy-see photos!

A spacious room features a plush king-sized bed centered on a decorative area rug. Dark-colored walls provide contrast to the light wooden flooring. A functional desk and chair are positioned by the window, with a small kitchenette area visible. A bathroom door is seen in the background.

Apartment in Great Barrington

4.89 out of 5 average rating, 159 reviews

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, 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

A view from a framed window reveals a cozy living space featuring a vintage wood-burning stove. A green sectional sofa provides seating, complemented by a light wood coffee table. Natural light fills the room, highlighting the open layout connecting to the kitchen area.

Cottage in Becket

4.9 out of 5 average rating, 113 reviews

Stylish Shales Brook Cottage-Cozy up to happiness

Bright & inviting! Welcome to our charming cottage, a stylish 2-bedroom, 2-bath retreat by Shales Brook. Relax on cool evenings beside the vintage Malm wood-burning stove. Enjoy modern comforts with central air, a screened-in porch, and a deck overlooking the tranquil waters of Shales Brook. The soothing sounds of the brook enhance your stay.. Located near fabulous Berkshire attractions, fantastic hikes, 15 minutes to the town of Lee, minutes to Jacob‘s pillow and 20 minutes to Tanglewood,!

Top guest favorite

A spacious deck overlooks a calm body of water, flanked by lush greenery and rocky cliffs. Two comfortable lounge chairs are positioned on a light-colored rug, accompanied by a small table and metal chairs, inviting relaxation while enjoying the natural scenery.

Place to stay in Leeds

4.98 out of 5 average rating, 166 reviews

The Ice House on Mill Pond

Escape to this picturesque setting nestled along the Catskill Creek, with private deck and awe-inspiring views of the pond, cliffs and rapids. Whether seeking a serene romantic getaway or a chance to recharge, this unique spot provides a harmonious blend of comfort and nature. Immerse in the soothing flow of nature and indulge in some of the best offerings in the Hudson Valley. Inside, the house is clean and cozy, providing the ideal haven to unwind and reconnect with your surroundings.

A dining area features a wooden table surrounded by four black chairs. A vase with greenery is centered on the table. In the background, a cozy seating area with a sofa is visible, illuminated by natural light from a nearby window.

Guesthouse in Housatonic

4.95 out of 5 average rating, 141 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.

A bright living area is observed, featuring cozy seating arrangements with a mix of chairs and a sofa. A television is mounted on the wall, while sliding glass doors provide views of the surrounding nature. A gas fireplace adds warmth, and a decorative rug enhances the space.

Home in Kingston

4.97 out of 5 average rating, 111 reviews

Hillside Views in Hudson Valley

Escape to this modern, cozy retreat where nature surrounds you. Fall asleep to owls, crickets, and frogs. Just 2 mins from Rosendale and a short drive to Kingston, New Paltz, and Stone Ridge, with restaurants and trails nearby. Enjoy a gas fireplace, a reading nook with treetop views, and a large deck that feels like you’re in the trees. The private outdoor space includes a fire pit, all on a serene 3-acre lot offering total peace and quiet. Your perfect Hudson Valley escape awaits!

An open, airy space features a wooden staircase leading to the upper level. A small dining area includes a table and two stools, while a comfortable seating area is visible in the background. Natural light filters through large windows, illuminating the modern design.

Vacation home in Great Barrington

4.94 out of 5 average rating, 239 reviews

Home in Great Barrington. Steps from downtown!

First Things First… Let’s Keep the Love Alive! ❤️ 🙌 Central and Private! Just steps away from historic downtown Great Barrington. East Mountain Hiking trails are a quick walk away. Enjoy sunset views with friends and family, before you walk into town for a night out! Butternut Ski Area: 5-10 min drive(traffic depending) Tanglewood: 20-25 min This new home features all new appliances and furniture. Enjoy luxury, charm, and privacy while you rest easy at The Maple. 🫶

Top guest favorite

A circle of wooden Adirondack chairs surrounds a fire pit, situated on a sandy area near the riverbank. Lush greenery and trees frame the space, while a modern two-story house can be seen in the background, blending with the natural landscape.

Apartment in Coxsackie

5 out of 5 average rating, 128 reviews

Hudson River Beach House

Explore all the activities the Hudson Valley has to offer and then relax in a room full of windows overlooking the Hudson River. Make a meal in the full kitchen or hang out by the beach, build a fire, play lawn games, read a book or float in the river. For you early risers, the sunrises are spectacular. This 1860 river house is 1/2 mile from the charming Village of Coxsackie NY and a central location to many great destinations such as Hudson, Woodstock, Athens, and Catskill.

Top guest favorite

A modern farmhouse bungalow is nestled among lush greenery along a brook. The red exterior is complemented by white trim and a front porch. A wooden bench sits by the water's edge, inviting relaxation amidst the tranquil natural surroundings.

Bungalow in Egremont

4.99 out of 5 average rating, 109 reviews

3-bedroom Berkshire bungalow on 2.5 peaceful acres

Modern farmhouse bungalow with private bridge and brook! Offering privacy as well as nearby nightlife, set upon 2.5 acres of beautiful Berkshire landscape but only 7 minutes to downtown Great Barrington and a short drive to Catamount and Butternut ski area. Mountains, waterfalls, countless hikes and bike routes, farmers' markets, coffee shops, breweries, Shakespeare and Co, Tanglewood, and world-class restaurants all come together in this quintessential New England community.

Top guest favorite

A charming two-story home is set on a landscaped plot with a gravel driveway. A wooden staircase leads to the entry, flanked by vibrant flower beds. The natural backdrop features lush trees and a striking granite ledge, creating a peaceful and inviting outdoor environment.

Home in Great Barrington

4.99 out of 5 average rating, 127 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.

A backyard hammock is positioned on lush green grass, providing a comfortable resting space. In the background, a cozy cottage is visible next to a spacious deck furnished with outdoor seating. The surrounding trees offer a serene natural setting.

Home in Great Barrington

4.94 out of 5 average rating, 123 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. 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 are available!

Vacation rentals for every style

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Popular amenities for West Stockbridge patio rentals

Free parking on premises

Air conditioning

Apartment rentals with a patio

Top guest favorite

Apartment in Hudson

4.96 out of 5 average rating, 197 reviews

Studio Oasis nr Warren St w porch & yard

A cozy studio space features a full-size bed with a neutral comforter, a desk and chair set against a wall, and a small television mounted above a radiator. Natural light enters through a window, with patterned curtains framing the view. The bathroom doorway is visible in the background.

Apartment in Amenia

4.93 out of 5 average rating, 119 reviews

Amenia Main St Cozy Studio

Top guest favorite

A balcony deck is depicted with two blue Adirondack chairs facing a small round table. A floral centerpiece is placed on the table, which is accompanied by two glasses. The area is surrounded by lush green trees, creating a serene atmosphere.

Apartment in North Adams

4.99 out of 5 average rating, 118 reviews

Historic Victorian - Entire 3rd floor

A historic Greek Revival house is seen from the front yard, featuring a white facade complemented by green trees. A red door serves as a focal point, with several windows allowing natural light. The yard is bordered by a wooden fence and includes well-maintained grass.

Apartment in Coxsackie

4.93 out of 5 average rating, 145 reviews

Lovely 1 bedroom suite in historical house

Top guest favorite

A modern kitchen features a central island with bar stools, stainless steel appliances, and white cabinetry. Natural light floods the space through a skylight and large windows, highlighting the open layout. A dining area with dark chairs sits adjacent to the kitchen.

Apartment in Charlemont

4.99 out of 5 average rating, 168 reviews

Suite 23 - Spacious Sunny 2-BR with Mountain view

A spacious living area is illuminated by natural light from large windows. A comfortable sofa is positioned beside a wooden coffee table. A raised dining area is visible, furnished with two chairs and a small table. The kitchenette features open shelving and rustic accents.

Apartment in Catskill

4.9 out of 5 average rating, 252 reviews

Catskill Village House - Mountain View Studio

Top guest favorite

A cozy bedroom features a spacious bed with layered bedding. A gallery wall of framed art pieces adds visual interest. Natural light filters through a window with shutters, illuminating the warm wood floors. An electric fireplace and a potted plant provide a touch of comfort.

Apartment in Kingston

4.97 out of 5 average rating, 293 reviews

The Ivy on the Stone

A lush, green lawn gently slopes toward a small pond, framed by trees on either side. The natural foliage provides shade and privacy, while a stone is visible among the undergrowth. The area is serene, inviting reflection and connection with nature.

Apartment in Otis

4.96 out of 5 average rating, 114 reviews

Enjoy every season the Berkshires have to offer.

House rentals with a patio

An aerial view captures the tranquil lakeside retreat surrounded by lush greenery. The house is positioned near the water, offering easy access to the scenic lake, which is nestled within a rich landscape of trees and foliage.

Home in Great Barrington

4.97 out of 5 average rating, 62 reviews

Waterfront Modern Lake Mansfield Retreat

A hot tub is positioned outdoors on a wooden deck, surrounded by tall trees. Fresh towels are neatly arranged on a small table nearby. The serene lake, framed by lush greenery, is visible in the background, indicating a peaceful outdoor retreat.

4.95 out of 5 average rating, 63 reviews

Stunning Fall Views! Hot Tub/Movie Room/Game Room

The farmhouse exterior displays a yellow façade with white trim and bright blue front door. Multiple large windows allow natural light to fill the home. A small seating area with two chairs and surrounding greenery adds to the inviting appearance of the property.

Home in Cornwall

4.99 out of 5 average rating, 127 reviews

The Farmhouse

An open kitchen and dining area feature a wooden dining table surrounded by black chairs. The space is illuminated by natural light from large windows, with a breakfast bar visible in the background. A neutral color palette adds warmth to the inviting layout.

Home in Pittsfield

4.93 out of 5 average rating, 105 reviews

Net Zero home with rustic Berkshire charm

The exterior of a transformed church features a pointed steeple and a central double door framed by a decorative arch. Stained-glass windows are visible, adding a historic charm against the dark wood siding. The surrounding area is lined with trees, hinting at the serene natural setting.

Home in Great Barrington

5 out of 5 average rating, 14 reviews

Berkshires Black Abbey

A bright living area features a yellow couch and two accent chairs, inviting relaxation. A patterned area rug centers the space, while natural light filters through large windows. A staircase is visible in the background, along with decorative plants and artwork adorning the walls.

Home in Pittsfield

4.95 out of 5 average rating, 191 reviews

Cantabile life in the Berkshires

An industrial-style staircase with a sleek metal railing offers a modern touch to the space. Rustic exposed brick walls complement the wooden flooring. A round dining table and light-filled windows create a welcoming atmosphere in the open layout.

Home in Catskill

4.94 out of 5 average rating, 115 reviews

Catskill Cottage | Walk to Downtown & River Views

4.93 out of 5 average rating, 30 reviews

Secluded Mountain and Lake View in Canaan, NY

Condo rentals with a patio

A well-lit bedroom features a spacious bed covered in neutral bedding. A wooden dresser and a small nightstand with a lamp are positioned beside the bed. Natural light streams through a round window highlighting the warm wood floors.

Condo in Litchfield County

4.96 out of 5 average rating, 26 reviews

Meadow View

A spacious living area features an arrangement of dark leather seating and a wooden dining table. Natural light streams through sliding glass doors that open to a balcony. A stone fireplace adds character, while decorative plants and artwork enhance the inviting ambiance.

Condo in Hancock

4.95 out of 5 average rating, 61 reviews

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

A dining area features a light-colored table with four wooden chairs, complemented by a decorative fruit bowl. Exposed brick walls add character, while soft lighting from nearby lamps creates a bright and inviting atmosphere. A comfortable living space is also visible in the background.

4.93 out of 5 average rating, 43 reviews

Spacious 3 bedroom apt in Lenox historic downtown

A cozy bedroom setting features a spacious bed with a patterned coverlet. A television is positioned across from a comfortable seating area with cushions. A writing desk with a lamp is placed near a window adorned with patterned curtains, allowing soft natural light to enter the room.

Private room in Saugerties

4.87 out of 5 average rating, 198 reviews

Hudson Valley Hiker’s Loft-Private Room Queen Bed

A comfortable living room is presented with two sofas adorned with festive cushions. A coffee table is centered on a cozy area rug, while a television sits atop a media console. Large windows framed by dark curtains allow natural light to fill the space.

Condo in Hancock

4.89 out of 5 average rating, 35 reviews

Unique - Country suite @ Jiminy Peak

A view of a downtown street, featuring a sidewalk lined with chairs and tables outside a café. Red accents can be seen on the café's exterior. Buildings of varying heights line the street, with greenery visible in the background under a cloudy sky.

4.73 out of 5 average rating, 48 reviews

Downtown Adams Vintage Getaway

Top guest favorite

A private bedroom is presented with a spacious bed covered in dark blue bedding. Soft light from a bedside lamp illuminates the room. A small wooden desk and chair are positioned near a window, which is adorned with light curtains allowing natural light to filter through.

Private room in Troy

4.92 out of 5 average rating, 13 reviews

Cozy private bedroom in 2nd floor apartment

Top guest favorite

A panoramic view captures the snowy landscape from the condo, showcasing ski trails on the mountains in the background. The foreground features a plaza with chairs arranged around a fire pit, with skiers and snowboards visible along the paths.

Condo in Hancock

4.98 out of 5 average rating, 47 reviews

SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit2

Quick stats about vacation rentals with a patio in West Stockbridge

Total rentals
50 properties
Nightly prices starting at
R2,957 ZAR before taxes and fees
Total number of reviews
1.5K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace

Destinations to explore