Holiday rentals with a patio in Stockbridge

4.94 out of 5 average rating, 110 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

Be a part of the solution in our centrally located solar home that sits on a safe and quiet street just a walk, ride, or drive from downtown Pittsfield! Warm up your day on the screened-in sun porch. Warm up your toes on the heated tile floors! Enjoy custom concrete counters and wood floors in this open kitchen concept. Grill out on the rear patio while your dogs roam in the enclosed backyard. Hiking trails abound and playgrounds are just a stroll away. We are emissions free! How cool is that?!

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.

4.94 out of 5 average rating, 125 reviews

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!

Guest house in Cummington

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.

5 out of 5 average rating, 140 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!

4.93 out of 5 average rating, 162 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.

4.9 out of 5 average rating, 115 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,!

5 out of 5 average rating, 101 reviews

A spacious great room features a stone fireplace amidst large windows, allowing natural light to fill the space. A wooden dining table is placed near a comfortable sectional sofa, creating an inviting area for relaxation and dining. The warm wood beams add a rustic touch.

Home in Staatsburg

Boulder Tree House

Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

Guest house in Housatonic

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.

4.95 out of 5 average rating, 151 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.

4.92 out of 5 average rating, 132 reviews

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.

Flat in Great Barrington

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" TV w/ Hulu + Live

4.97 out of 5 average rating, 116 reviews

A spacious living room is highlighted by a comfortable green couch adorned with decorative pillows. A sleek coffee table is centered within the space, while a relaxed dog lies on the soft, natural fiber rug, contributing to the inviting atmosphere.

Home in Saugerties

Waterfront, Dog & Family Friendly, Cozy Cottage

El Girasol, "The Sunflower," a sunny, family and pet friendly cottage on the Esopus Creek in the Catskill Mountains. Our home is fully furnished with global & vintage finds. This charming cottage has 2 beds, spacious living room with a big, comfy sleeper sofa and cozy electric fireplace & fully equipped kitchen combined with a dining room. Creek access, BBQ, fire pit, fenced in backyard, & 2 decks makes our home a great destination for a relaxing getaway with family, friends and pets.

Holiday 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, 244 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. 🫶

4.98 out of 5 average rating, 115 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.

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.

4.99 out of 5 average rating, 135 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.

Popular amenities for rentals with patio in Stockbridge

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Flat rentals with a patio

4.97 out of 5 average rating, 206 reviews

Flat in Hudson

Studio Oasis nr Warren St w porch & yard

4.92 out of 5 average rating, 125 reviews

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.

Flat in Amenia

Amenia Main St Cozy Studio

4.99 out of 5 average rating, 122 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.

Flat in North Adams

Historic Victorian - Entire 3rd floor

Superhost

A well-lit patio space features a wooden table with a gas fire pit at its center, surrounded by four wicker chairs. Natural stone walls and a flower-adorned fence provide a backdrop, while soft lighting enhances the cozy atmosphere.

Flat in Saugerties

4.92 out of 5 average rating, 363 reviews

Saugerties Village home with great backyard!

4.99 out of 5 average rating, 171 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.

Flat in Charlemont

Suite 23 - Spacious Sunny 2-BR with Mountain view

4.91 out of 5 average rating, 267 reviews

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.

Flat in Catskill

Catskill Village House - Mountain View Studio

4.92 out of 5 average rating, 131 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.

Flat in North Adams

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

4.99 out of 5 average rating, 132 reviews

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.

Flat in Coxsackie

Hudson River Beach House

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.

4.97 out of 5 average rating, 64 reviews

Waterfront Modern Lake Mansfield Retreat

4.96 out of 5 average rating, 68 reviews

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.

Home in Canaan

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

5 out of 5 average rating, 45 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

Berkshire’s Best-hottub-fitness/gameroom

4.93 out of 5 average rating, 28 reviews

The exterior of the cottage is framed by lush greenery, with a wooden trellis adorned with vibrant purple flowers. Sunlight filters through the surrounding trees, highlighting the soft colors of the house and creating a tranquil atmosphere.

Home in Lenox

Lenox Cottage

4.98 out of 5 average rating, 66 reviews

The exterior of a historic red house is surrounded by lush green grass and trees. A stone path leads to the front entrance, while flowering plants add a touch of color to the landscape. The sky is clear with some clouds, creating a serene outdoor setting.

Home in Old Chatham

The Red House

4.97 out of 5 average rating, 100 reviews

A wooden house is set against a wooded backdrop, featuring a dark facade with large windows. An outdoor fire pit is surrounded by seating arrangements on either side. The grassy area offers a natural and open invitation to enjoy the surrounding landscape.

Home in Catskill

Modern High-end 2BR2BATH in the woods of Catskills

4.97 out of 5 average rating, 66 reviews

The historic stone church exterior is framed by lush greenery and a manicured lawn. Towering above, the bell tower features intricate architectural details. A wooden fence surrounds the property, leading to a pathway that invites exploration of the beautiful grounds.

Home in Lanesborough

Historic Stone Church in The Berkshires

Apartment rentals with a patio

Apartment 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, 29 reviews

Meadow View

4.95 out of 5 average rating, 62 reviews

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.

Apartment in Hancock

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