Vacation rentals with a patio in Stockbridge

Guesthouse in Stockbridge

The exterior of the wooden cottage is showcased, featuring a large gray facade with three prominent windows. A deck extends from the front, complemented by outdoor seating and a patio umbrella. Lush greenery surrounds the property, enhancing its rustic charm.

4.93 out of 5 average rating, 42 reviews

Light-filled Carpenter's Cottage w/ EV charger!

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 and one can hear the ambient hum of the highway, there is ample privacy with a separate parking spot, walkway, landscaping, and a private deck. EV charger! The cottage sleeps 2 in the queen bed, but there is seating for a dinner party of 6. It sits on a south-facing hill, looking out towards Monument Mountain. You’ll love it!

4.95 out of 5 average rating, 128 reviews

A hot tub sits on a polished wooden deck, surrounded by greenery. Soft lighting from string lights illuminates the area. A colorful striped pillow rests on a lounge chair, with a patterned plate and drink placed nearby, creating a relaxing outdoor retreat.

Home in Great Barrington

Best of the Berkshires + Hot Tub by Evergreen Home

10 MINUTES TO CATAMOUNT 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!

5 out of 5 average rating, 148 reviews

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

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!

4.93 out of 5 average rating, 168 reviews

A spacious kitchen is equipped with white cabinetry and a large wooden island, featuring bar seating. Natural light floods the room through multiple windows. A dining table for six complements the space, with a fruit bowl as a centerpiece.

Cottage in Sheffield

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.

4.91 out of 5 average rating, 119 reviews

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

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,!

4.95 out of 5 average rating, 155 reviews

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

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.

Vacation home in Great Barrington

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.

4.94 out of 5 average rating, 255 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. 🫶

Apartment in Great Barrington

A modern bedroom is presented, featuring a plush king-sized bed with crisp white linens. A sliding glass door allows access to an outdoor space, while a small table and decorative items add to the aesthetic. A dark accent wall provides depth, complemented by natural light.

4.89 out of 5 average rating, 141 reviews

King Bed |Wi-Fi| 2m to 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 KEY FEATURES: *MCM Design * Plush King Sized Bed w/ high end Centium Satin Linens *High Speed Internet *58" Smart TV

4.98 out of 5 average rating, 116 reviews

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

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.

4.97 out of 5 average rating, 29 reviews

A bright living area features large windows that allow natural light to flood in, showcasing views of nearby trees in autumnal colors. Two modern armchairs and a navy sofa are arranged on a patterned area rug, with a coffee table positioned centrally.

Home in Stockbridge

Stockbridge pied-à-terre

Enjoy our new in-town stylish pied-à-terre , a block from the Red Lion. Off the main thoroughfare just enough but an easy walk for a cocktail on the porch! a stand alone building, large open window filled living/kitchen area, small 2nd floor balcony with chairs to relax, spacious bdrm with king size bed, and a modern tiled bathroom. Central HVAC, great water pressure, all new everything and a well appointed kitchen. July and August are by the week rental only.

4.99 out of 5 average rating, 72 reviews

Cabin in East Nassau

Winter Cabin Hideaway - Views + Fire Pit + Hot Tub

Escape to your cozy mountain retreat—perfect for winter getaways! Just 15 mins to Jiminy Peak and close to Tanglewood, MASS MoCA & The Clark. Enjoy skiing and nights under the stars in the wood-fired hot tub. Warm up by the Breeo fire pit or inside with radiant floors, cook festive meals, and unwind in total privacy. With EV charging and a peaceful workspace, it’s the perfect spot to celebrate the Holidays and enjoy the winter season.

4.99 out of 5 average rating, 317 reviews

A tiny home features a private hot tub on the deck, illuminated by soft LED lights. The structure is surrounded by natural wood paneling, with doors leading into the cozy interior, where warm light spills out, creating an inviting ambiance.

Tiny home in Chatham

Boutique TINY home+private HOT TUB-walk to Main St

Blush & Bubbles for December stays. Romantic, boutique-luxe tiny home with private hot tub, firepit, and dreamy loft lounge. Plush queen bed, full kitchen, and curated charm throughout. A peaceful oasis just 2 mins from Chatham’s Main Street lined with restaurants, brewery, shops & theater. The perfect upstate NY getaway for couples—hike, visit galleries, stroll to dinner, or unwind in your own private spa oasis at @artparkhomes.

Popular amenities for Stockbridge patio rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with a patio

4.97 out of 5 average rating, 211 reviews

Apartment in Hudson

Studio Oasis nr Warren St w porch & yard

Superhost

A modern kitchen features stainless steel appliances, including a refrigerator and stove. Dark cabinetry contrasts with white tile backsplash, while natural light fills the space through multiple windows. A dining area is visible with a dark table and a view of the hallway leading to the entrance.

Apartment in Melrose

4.81 out of 5 average rating, 88 reviews

Newly Renovated Gem in Melrose - Pet Friendly

4.99 out of 5 average rating, 125 reviews

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

Historic Victorian - Entire 3rd floor

4.93 out of 5 average rating, 151 reviews

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

Lovely 1 bedroom suite in historical house

4.99 out of 5 average rating, 172 reviews

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

Suite 23 - Spacious Sunny 2-BR with Mountain view

4.93 out of 5 average rating, 182 reviews

A cozy bedroom features a spacious bed with light grey bedding, accompanied by a side table and a soft glow from a nearby lamp. Sunlight filters through sheer white curtains, illuminating the warm wood floor. A doorway leads to the private bathroom, visible on the right.

Apartment in Catskill

Catskill Village House - Studio w/ Private Terrace

5 out of 5 average rating, 32 reviews

The living room features a sectional couch in a neutral fabric, arranged invitingly around a coffee table. A flat-screen TV is positioned on a media console across from the seating area. A dining table with chairs and a hutch filled with tableware are visible in the background.

Apartment in Chatham

Kinderhaus Loft in Chatham, New York

4.9 out of 5 average rating, 134 reviews

A welcoming bedroom features a spacious bed with a light duvet and decorative pillows. A wooden dresser stands beside the bed, and natural light filters through a window adorned with light curtains. Soft wooden flooring enhances the room's warm ambiance.

Apartment in North Adams

Frankie’s Place - A Mass MoCA Neighborhood 2BR APT

House rentals with a patio

4.97 out of 5 average rating, 67 reviews

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

Waterfront Modern Lake Mansfield Retreat

4.94 out of 5 average rating, 113 reviews

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

Net Zero home with rustic Berkshire charm

5 out of 5 average rating, 47 reviews

A spacious open-plan living area is showcased, featuring large windows that invite natural light. A modern sectional sofa in warm tones is arranged around a low table. A dining area with a long table and dining chairs is visible in the background, enhancing the inviting atmosphere.

Home in Egremont

The Catamount Ski Haus with Pool & Hot Tub

5 out of 5 average rating, 6 reviews

Home in Great Barrington

Berkshire’s Best-hottub-fitness/gameroom

4.96 out of 5 average rating, 172 reviews

A spacious cedar hot tub sits peacefully outdoors, surrounded by a natural setting of trees and open space. Bubbles rise from the water, creating a relaxing atmosphere. Clear blue skies are visible above, enhancing the tranquil environment.

Home in Hudson

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

4.95 out of 5 average rating, 202 reviews

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

Cantabile life in the Berkshires

4.97 out of 5 average rating, 183 reviews

A cozy living room features floral-patterned armchairs and a sofa, complemented by a low coffee table. A lamp provides soft lighting, and artwork hangs on the walls, enhancing the warm decor. A textured rug covers the floor, adding comfort to the space.

Home in Catskill

Cheerful Catskill Village Cottage

4.94 out of 5 average rating, 122 reviews

The exterior of the Catskill Cottage showcases rustic brick walls and a distinctive green metal roof. A landscaped area with shrubs is visible in the foreground, along with a stone bench positioned near the entrance. The building is surrounded by a gravel pathway on a sunny day.

Home in Catskill

Catskill Cottage | Walk to Downtown & River Views

Condo rentals with a patio

An inviting indoor pool area is surrounded by large windows that provide a view of the outdoors. Lounge chairs line the poolside, and natural light fills the space, highlighting the tiled flooring and gently rippling water.

5 out of 5 average rating, 4 reviews

Ski Jiminy Peak - 1BD

Condo in Litchfield County

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.

4.93 out of 5 average rating, 30 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.

4.95 out of 5 average rating, 62 reviews

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

4.93 out of 5 average rating, 45 reviews

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.

Condo in Lenox

Spacious 3 bedroom apt in Lenox historic downtown

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.

4.89 out of 5 average rating, 35 reviews

Unique - Country suite @ Jiminy Peak

Superhost

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.

Condo in Adams

4.71 out of 5 average rating, 55 reviews

Downtown Adams Vintage Getaway

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.