Vacation rentals with a patio in Williamstown

5 out of 5 average rating, 101 reviews

A white farmhouse with a spacious front porch features rocking chairs and a welcoming front yard. A friendly dog is seen sitting on the green grass, surrounded by autumn foliage. The structure's windows and a gabled roof enhance its charming exterior.

Home in Bennington

Vermont Farmhouse •Walk to Village & Hiking Trails

Experience the magic of this lovingly restored 1860s Vermont farmhouse, where historic charm blends seamlessly with modern living. Set on 1 acre with 1700 sq ft of thoughtfully designed space, enjoy 2 cozy bedrooms, 2.5 baths, and sun-filled common areas made for unwinding. Sip coffee in Adirondack rockers on the expansive front deck, explore 280 acres of woodland trails steps away, stroll into the village, then gather at the fire pit for s'mores under the stars. Welcome to The Vermont Farmhouse

4.85 out of 5 average rating, 164 reviews

The custom home features warm wood siding and a welcoming porch with flower boxes. A spacious deck with rustic railings extends from the second floor, while a covered area includes seating. Surrounding greenery enhances the natural setting, creating a serene outdoor ambiance.

Cabin in Wardsboro

Mountain side acres

10 years of love and affection went into building our 2 bedroom custom home. Sticking with natural products to blend together the beauty of the surrounding area. Lay in bed at night and listen to river that runs the entire length of the property. The house has a full kitchen with seating for 6. Spacious living room for relaxing or admiring one of the many birds that visit all year round. Two upstairs bedrooms and office space. Walkout basement with full entertainment area, hot tub,exercise room.

4.93 out of 5 average rating, 119 reviews

A chalet-style home is surrounded by lush greenery, featuring a large three-sided wrap-around deck. Tall windows dominate the front, allowing ample natural light. To the side, a wooden garage complements the main structure, set against a backdrop of trees and an expansive lawn.

Chalet in Stamford

Peaceful VT Chalet w/ Mountain View’s

My peaceful 3-bedroom chalet has everything you need for your VT trip. The house comes with a washer, dryer, Roku TV’s, pullout queen couch. 2.5 bathrooms, indoor elec. fireplace, outdoor fire pit and fully equipped kitchen.Short driving distance to several popular golf courses, shops, restaurants, breweries, fishing, white water rafting, hiking, kayaking, ATV/snowmobile trails, & mountain slopes. An ideal base to explore the Green Moutain National Forests (VT) or the Berkshire Mountains (MA).

5 out of 5 average rating, 159 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!

4.89 out of 5 average rating, 183 reviews

The inviting living area features intricate wood detailing and an ornamental ceiling. Two comfortable armchairs flank a round marble coffee table, positioned over a traditional area rug. A decorative fireplace and a flat-screen TV offer cozy amenities, while natural light fills the space through nearby windows.

Home in North Adams

Art House! W Hot Tub By Mass Moca

This newly renovated Victorian curated by the local Grant Larkin Design Team is a great space for large groups, with easy access to Berkshire Art Museum & outdoor fun! Nearby: Mass Moca 2 min Big Y 2 min MCLA 5 min Clarksburg State Park 7 min Hairpin Turn 8 min Williams College 10 min Susan B Anthony Museum 12 min Ashuwillticook Rail Trail 13 min Clark Art Institute 14 min Mt. Greylock Gould Trailhead 14 min Mohawk State Forest 23 min Jiminy Peak Resort 29 min Bright Ideas Brewing 2 min

4.94 out of 5 average rating, 174 reviews

A spacious mountain lodge is depicted, featuring a striking stone chimney and expansive decks. Large windows frame the scenic landscape, while lush green grass surrounds the building. The warm tones of the log exterior harmonize with the natural setting, inviting outdoor relaxation.

Apartment in North Adams

Berkshire Mountain Top Chalet

Amazing mountain top lodge with beautiful views, and majestic log interior. Soaring ceilings, dramatic stone fireplace, and many more amazing amenities such as blazing fast internet, multiple decks, and hot tub. This gorgeous lodge is located near all The Berkshires has to offer—resplendent nature with waterfalls, hiking trails; cultural institutions such as Mass MoCA, and the Clark Institute; adventures such as zip-lining, white-water rafting, and skiing—it is the ultimate place for you.

4.95 out of 5 average rating, 203 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

Relax with your family and friends after a day of skiing, hiking or a night of Tanglewood concert in this newly renovated home at the center of the Berkshires. Located in a quiet and friendly neighborhood, our home is 5min to Pontoosuc Lake and Lake Onota, 10min to Bousquet, 15min to Mt Greylock, 20min to Jiminy Peak and Tanglewood. Multiple grocery stores and shopping centers near by. Child/baby friendly, we have books, games, PingPong, foosball and a grand piano. Musicians are welcome!

4.82 out of 5 average rating, 118 reviews

A white two-story house sits at the intersection of a quiet street, surrounded by vibrant autumn foliage. A well-maintained yard features a mix of mature trees, with golden and orange leaves contrasting against the blue sky. A leaf-covered path leads toward the entrance.

Loft in Bennington

1 bedroom guest house on dead-end rd

Enjoy a peaceful and private space with 1 bedroom, 1 bath, full kitchen and on site parking. Last house on a dead end rd. 5 min from Southwestern VT Medical Center. 40 min from Mount Snow. 25 min from MassMoca. 15 min walk to Main St where you can enjoy great food and shops. No smoking on premises. Please note there is stairs separating the bedroom (downstairs) and living area, bathroom, and kitchen (upstairs). The stairs are steep and may be difficult for some people.

4.89 out of 5 average rating, 166 reviews

The exterior of a charming yellow cottage is visible, featuring dark green shutters and a welcoming porch with decorative elements. A well-kept garden with colorful flowers and greenery surrounds the cottage, while a gravel pathway leads to the entrance under a partly cloudy blue sky.

Cottage in Monroe

Pumpkin Pine Cottage: your next adventure awaits!

Explore the Deerfield River Valley and Hoosac Range from this tranquil base. Close to skiing, snow tubing, snowshoeing, hiking, birding, kayaking, white-water rafting, fly fishing, zip lines, and more. Like bikes? Amazing gravel, road, and MTB offerings await. Seek culture? Mass MOCA, Clark Art Institute, Northampton, Shelburne Falls, and the Berkshires are a short drive away. Covered bridges, farm stands, sugar shacks, and waterfalls are too plentiful to count!

4.98 out of 5 average rating, 127 reviews

A bright living area is highlighted by large windows offering expansive mountain views. A colorful abstract artwork hangs against a brick wall, framed by a green houseplant. A wooden coffee table sits atop a patterned rug, complemented by a cozy sofa and a wall-mounted TV.

Cottage in Williamstown

Artistic Nature Cottage

Kalarama Cottage is a newly renovated space in the middle of nature! Make yourself right at home in this quiet, private and peaceful location. The cottage is overlooking a beautiful forested mountain range, with easy access to hiking, biking, and cross-country ski trails right out the door. Kalarama is bright and sunny with stunning views. Come to unwind, enjoy nature, read, meditate or just work remotely from our 23 acre property!

4.9 out of 5 average rating, 136 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

Experience North Adams with unbeatable convenience! This centrally located apartment puts your whole group just a short walk or bike ride away from Mass MoCA, the farmer’s market, and the shops and restaurants on Main Street. Enjoy stress-free access to all the local attractions—no parking hassles, just easy, enjoyable days exploring the best of North Adams. Perfect for your next Mass MoCA event or weekend getaway!

4.92 out of 5 average rating, 225 reviews

A classic log cabin stands surrounded by greenery, featuring a spacious front porch with a wooden railing. Large windows dominate the front, allowing natural light to fill the interior. An American flag is displayed, adding to the rustic charm of the structure.

Cabin in Plainfield

Peaceful Cabin in the Woods

Escape the noise and come relax in the middle of the beautiful Berkshire Hills. This classic log cabin has been recently renovated so that you can unwind and connect to the picturesque landscape that envelopes this property. You can drive 30 minutes west to North Adams and visit Mass Moca or 30 minutes east to Northampton, Amherst & Hadley. (Please note, 1/2 of the bedrooms is an open loft).

Popular amenities for Williamstown patio rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with a patio

4.5 out of 5 average rating, 70 reviews

Apartment in Adams

Apartment on the Bike Trail, in the heart of Adams

4.99 out of 5 average rating, 177 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

4.96 out of 5 average rating, 92 reviews

The exterior of a two-story purple house is featured, showcasing a wrap-around porch with white rocking chairs and a small table. Large windows allow ample natural light, while a green planter hangs near the entrance, surrounded by lush foliage.

Apartment in North Adams

"Nostalgia" a spacious2 bedroom first floor unit.

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.

Apartment in Charlemont

Spacious apartment close to skiing and rafting

Apartment in Williamstown

A bright dining area features a round white table surrounded by four green chairs. Natural light floods the space through two windows, adorned with light-filtering shades. The warm wooden floor complements the modern decor, creating an inviting atmosphere for meals and gatherings.

5 out of 5 average rating, 33 reviews

Downtown Jewel | Stylish | Fully Stocked | Firepit

5 out of 5 average rating, 27 reviews

A Bentwood rocking chair with an elegant curved design is positioned in front of a colorful quilt featuring geometric patterns. The chair's natural cane backrest and wooden frame contrast with the vibrant hues of the quilt, enhancing the cozy atmosphere of the space.

Apartment in New Lebanon

Folk Art Studio: 1-bedroom near the Berkshires

4.95 out of 5 average rating, 64 reviews

A spacious living area features a sectional sofa in muted green, paired with a brown leather recliner. Natural light fills the room through large windows, and a painting adds a touch of color to the light walls. A circular table is situated in front, with a textured area rug underfoot.

Apartment in Pittsfield

Modern Gem in the Heart of Berkshires

4.82 out of 5 average rating, 45 reviews

A grassy area is presented with two black metal benches positioned on either side of a small garden. Lush trees and vibrant greenery surround a historic colonial-style mansion, which is visible in the background against a clear sky.

Apartment in Troy

Charming Hudson riverfront 1BR

House rentals with a patio

4.95 out of 5 average rating, 115 reviews

A charming colonial home is depicted, featuring white siding and a green front door. Potted flowers decorate the entryway, and several windows provide natural light. The well-maintained lawn is surrounded by colorful blooms, contributing to the home's inviting curb appeal.

Home in Kinderhook

Modern and cozy 3 bedroom with outdoor oasis

4.94 out of 5 average rating, 115 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

4.93 out of 5 average rating, 100 reviews

A cozy cabin is presented, featuring a wraparound deck and surrounded by lush greenery. Trees with autumn foliage add splashes of color to the landscape. The structure is elevated, inviting guests to enjoy the view from the deck.

Home in Dover

Cozy Riverfront Home, 1mi to Mt Snow, On Moover

5 out of 5 average rating, 31 reviews

A charming two-story home is set amidst lush greenery, featuring a spacious front porch with seating. The house is flanked by trees, and a large lawn is visible in front, complemented by a gravel driveway leading towards an attached garage.

Home in Lanesborough

Berkshire Mountain House

4.82 out of 5 average rating, 17 reviews

A welcoming entrance features a blue rocking chair placed on a covered porch. Bright flowers hang from the ceiling, while a flower pot filled with sunflowers stands beside the chair, adding a cheerful touch to the home’s facade.

Home in North Adams

Cozy Berkshire Cottage House-private fenced yard

5 out of 5 average rating, 20 reviews

A vibrant outdoor space is visible, showcasing a spacious lawn surrounded by well-maintained gardens and trees. The home itself features a combination of yellow siding and natural materials, with multiple windows and an inviting entrance leading to the patio area.

Home in Williamstown

Beautiful, cozy house for rent

4.93 out of 5 average rating, 73 reviews

Home in Adams

Mount Greylock View Retreat,3 bedroom,2 1/2 bath.

4.88 out of 5 average rating, 42 reviews

Aerial view capturing a modern farmhouse cabin surrounded by vibrant autumn foliage. The landscape features a mix of lush trees in shades of orange, yellow, and green, with distant mountains visible under a clear blue sky. A dirt road borders the property.

Home in Pownal

Modern Farmhouse Retreat

Condo rentals with a patio

4.95 out of 5 average rating, 63 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.

Condo in Hancock

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

A cozy living area is highlighted by a stone fireplace, featuring firewood neatly stacked beside it. A flat-screen TV is mounted above the mantel, with built-in cabinets on either side. A sectional sofa and wooden coffee table provide comfortable seating for relaxation.

4.97 out of 5 average rating, 29 reviews

Slopes N Seasons | Trailside Condo at Mount Snow

5 out of 5 average rating, 9 reviews

Walk to Dining, Arcade & Bar- 5 Min to Mt. Snow

A cozy living area features a large sectional sofa and a wooden coffee table, set on a spacious area rug. Natural light filters through a large window, with a stone fireplace and a mounted television providing warmth and entertainment.

4.94 out of 5 average rating, 52 reviews

Ski On/Off 2BR w/Pool, Fireplace & Arcade

A spacious living area is introduced, featuring a stone fireplace and a large sectional sofa arranged around a coffee table. A dining table and chairs are positioned nearby, with natural light filtering through large windows adorned with curtains.

4.94 out of 5 average rating, 81 reviews

Ski in-out Seasons Condo on mtn-sports center-pool

A cozy living room showcases two plush couches and a small wooden coffee table. A gas stove is nestled in a brick corner, while sliding doors offer views of the outdoors. Colorful lights frame the window, adding a touch of charm to the space.

4.92 out of 5 average rating, 59 reviews

Ski Condo 5 Min from Mt Snow

5 out of 5 average rating, 54 reviews

A snow-covered landscape reveals nearby mountains and ski slopes under a clear blue sky. Trees with bare branches frame the scene, while quaint buildings and a parking area are visible in the foreground, suggesting a vibrant ski village atmosphere.

Condo in Stratton

Your Vermondo awaits: Steps to Lifts & Village.

A modern kitchen is showcased with white cabinets and a dark granite countertop. Stainless steel appliances, including a refrigerator and stove, are visible. A dining table with wooden chairs is situated nearby, while a cozy living area can be seen through the open layout.