Holiday rentals with a patio in Monterey

4.91 out of 5 average rating, 134 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

Cozy studio in well maintained house from 1900. 150 sq ft with full size bed. Unit is comfortable for one, tight for two. Right in small town of Amenia. Front porch with seats/table. Walking to food, shops, drive-in movie theatre, and rail trail. Trail is 1/4 mile from house, paved and only allows walking/biking. On trail: Arts village Wassaic (3 miles south) Millerton (8 miles north). Train to NYC is 2.5m south. Tons in area: wineries, distillery, lakes, hiking, theatre & quaint towns.

4.99 out of 5 average rating, 112 reviews

Cabin in Norfolk

The Red Cabin-Secluded Getaway with backyard Brook

Welcome to our secluded mid-century cabin nestled in the foothills of the Berkshires in Northwestern CT! When you stay here you'll find over three private acres of ferns, forests, wild flowers and a native trout brook a stone's throw from the backdoor with your private hot tub to relax in. Beyond the brook are hundreds of acres of state forest preserve. Enjoy great hiking, fishing, skiing, antiques and restaurants minutes away. Only 2 hours from NYC and 8 minutes to Historic Norfolk Center.

4.95 out of 5 average rating, 129 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!

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, 154 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!

4.94 out of 5 average rating, 172 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, 121 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,!

4.92 out of 5 average rating, 125 reviews

A modern bedroom features a spacious bed with high-end linens, flanked by two stylish chairs. A desk and chair sit by the window, and an arched door adds architectural interest. Natural light illuminates the room, highlighting a unique wall design in neutral tones.

Flat in Great Barrington

King Bed | Patio | 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 *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

4.99 out of 5 average rating, 145 reviews

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

The Farmhouse

Enjoy staying at our charming Farmhouse in the heart of our working dairy farm. Our farm sits on some of the most beautiful hills in Cornwall with the famous Gateway to Cornwall view where you can see our dairy cows grazing in the grandeur of nature. Come say hello to the cows in the barn during milking or watch the herd cross the road evoking sites you might expect to see in small European farming villages. You'll likely see us on our tractors bringing hay and water to our cows!

4.99 out of 5 average rating, 141 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

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.

4.98 out of 5 average rating, 117 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.

4.95 out of 5 average rating, 135 reviews

A light-filled living room features a gray sectional sofa with a colorful throw pillow. A wooden console table stands beside a lamp, while natural light enters through two large windows adorned with white trim, providing views of the surrounding greenery. Vintage art pieces are displayed on the walls.

Guest house in Sharon

Cottage with a Waterfall View

Fall asleep to the sound of a waterfall and babbling brook outside your bedroom window in this historic former flax mill known as St. John's Mill. The cottage is newly renovated and features a well equipped kitchen, sofa where you can put up your feet and gaze out the living room window at the dam and waterfall, and a private grill and terrace overlooking Guinea Creek. Located along a scenic route convenient to Kent, Millerton, Salisbury & Amenia.

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, 256 reviews

Home in Great Barrington. Steps from downtown!

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. 🫶

Popular amenities for rentals with patio in Monterey

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Flat rentals with a patio

4.97 out of 5 average rating, 211 reviews

Flat in Hudson

Studio Oasis nr Warren St w porch & yard

4.96 out of 5 average rating, 100 reviews

A serene bedroom features a spacious bed dressed in a light, textured coverlet. Two comfortable floral armchairs sit beside a dresser, complemented by a full-length mirror. Soft light filters through a window, illuminating the gentle pastel tones of the room.

Flat in Hillsdale

Ski at Catamount, Butternut, Walk to Brewery

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.

Flat in Coxsackie

Lovely 1 bedroom suite in historical house

4.99 out of 5 average rating, 174 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

5 out of 5 average rating, 33 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.

Flat in Chatham

Kinderhaus Loft in Chatham, New York

4.94 out of 5 average rating, 34 reviews

A wooden deck is shown with a low railing, surrounded by green grass and garden beds. Flower pots adorn the railing, while a small table stands on the side. The exterior of the building is gray, featuring a bright yellow door.

Flat in Red Hook

Hummingbird apt

5 out of 5 average rating, 40 reviews

A welcoming living space features a comfortable sofa and two chairs arranged around a circular coffee table. A television is positioned in front of the seating area, while a dining table with chairs is visible in the background. Textured rugs and wall art add character to the room.

Flat in Hudson

Townhouse apt+cntrl+prking+yrd

4.85 out of 5 average rating, 110 reviews

An open-concept living and dining area is featured, with a wooden dining table surrounded by white chairs. A decorative area rug lies underneath. The adjacent living room is visible, showcasing a brown sofa, two armchairs, and various decorative wall art, all in a soothing color palette.

Flat in Charlemont

Spacious apartment close to skiing and rafting

House rentals with a patio

4.9 out of 5 average rating, 50 reviews

A spacious bedroom features a large bed adorned with white linens and decorative pillows. A warm fire crackles in a brick fireplace, complemented by wooden beams overhead. Soft lighting is provided by two bedside lamps, and a colorful area rug adds a touch of vibrancy to the room.

Home in Great Barrington

Cozy. Clean. Free bagel shop.

5 out of 5 average rating, 92 reviews

The charming exterior of a renovated farmhouse features a spacious front porch with a red bench and hanging flower baskets. Large windows allow natural light to fill the entryway, while lush green grass and trees frame the property.

Home in Canaan

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove

4.88 out of 5 average rating, 8 reviews

A cozy living room features a light grey sofa adorned with patterned cushions. A wooden trunk serves as a coffee table in front of the sofa. Natural light filters through a skylight, highlighting the warm red walls and floral arrangement on a side table.

Home in Norfolk

entire farm style house

4.87 out of 5 average rating, 31 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

4.99 out of 5 average rating, 71 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

4.96 out of 5 average rating, 145 reviews

A charming red cottage is surrounded by trees displaying autumn foliage. The structure features white trim and a star accent on the wall. A fenced garden area lies in front, complemented by neatly arranged shrubs. A driveway leads to the entrance, enhancing accessibility.

Home in Amenia

The Red Country Cottage

4.85 out of 5 average rating, 111 reviews

A cozy wooden cabin is surrounded by lush greenery, featuring a welcoming porch with a sturdy railing. Sunlight casts gentle shadows across the textured facade, showcasing the natural wood shingles and spacious windows. A well-kept lawn enhances the inviting atmosphere.

Home in Cornwall

State Forest Getaway

4.94 out of 5 average rating, 16 reviews

Home in Great Barrington

Lovely house in the Berkshires

Apartment 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

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, 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, 63 reviews

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

4.91 out of 5 average rating, 46 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.

Apartment 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

4.71 out of 5 average rating, 55 reviews

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.

Apartment in Adams

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.