Holiday rentals with outdoor seating in Wilmington

4.97 out of 5 average rating, 140 reviews

The entryway features a welcoming entrance with a wooden door, adorned with a green wreath. A glimpse into the bright interior reveals modern seating and natural light streaming through large windows, enhancing the inviting space that awaits inside.

Chalet in Wilmington

Snug Chalet - Wi-Fi + Close to Mount Snow

This stylish 1971 chalet is a country retreat with modern comforts for you and your family... complete with strong WiFi and a fenced-in dog yard! The minimal cabin is tucked in the trees and set up for families and friends, pet & kid-friendly. 10-15 Minutes to Mount Snow 10-15 Minutes to Downtown Wilmington This is a country house, not a boutique hotel :) If booking during winter or spring months, we HIGHLY recommend a 4wd vehicle as the weather can cause some tough road conditions (snow/mud).

4.91 out of 5 average rating, 253 reviews

A bathroom features natural wood paneling and a brick accent wall. A compact vanity with a sink is complemented by a mirror and overhead lighting. Shelves hold neatly folded towels, while a washer and dryer unit is integrated into the design, presenting a functional space.

Home in Wilmington

Wilmington A-Frame- Cozy and Convenient

Entire charming and chic A-frame chalet conveniently located to all the amenities Wilmington has to offer. Walk into town to enjoy dining, shopping and trail hiking or take a short 15 minute drive to Mount Snow for a day of outdoor adventure. Relax on the water at Harriman Reservoir, just a 2 mile drive from the house. House is also conveniently located along the Moover route. Relax back at the house while enjoying time on the front porch or an evening on the couch. Located on Main Street.

4.94 out of 5 average rating, 138 reviews

A bright living space is surrounded by floor-to-ceiling windows, offering views of vibrant foliage and serene waterways. A small wooden table is positioned on a natural wood floor, highlighting the connection to the outdoor landscape. Warm sunlight filters through the trees, creating a calm ambiance.

Home in Guilford

Vermont Mirror House

Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

4.88 out of 5 average rating, 186 reviews

The outdoor pool is surrounded by a chain-link fence and features a concrete deck. Sun lounges and chairs are positioned nearby, with a colorful beach towel draped over a lounge chair. Lush greenery frames the area, providing a serene setting.

Home in Wilmington

Adams Farm-"The Little Farmhouse"

A Clean Ranch style home with hardwood floors located on a 100-acre Historic Vermont Farm. Retired farmers live in separate farmhouse & are available throughout your stay. Conveniently located just minutes away from MT Snow Ski Resort, Hermitage Resort, Stratton Mt. for Skiing, Snowboarding, Tubing, Hiking & Mountain Biking. 3 miles from downtown Wilmington. Minutes to public beaches and lakes. Use our trails for snowshoeing, X-Country Skiing or hiking. Our Pool is avail July -Labor day

4.99 out of 5 average rating, 377 reviews

Tiny home in Wilmington

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

4.91 out of 5 average rating, 152 reviews

A comfortable living area features a dark leather sofa with two accent pillows and a coffee table atop a patterned rug. A dining table with four chairs is positioned nearby, and natural light enters through a window dressed with light curtains. Wall decor includes vintage skis and decorative deer antlers.

Apartment in Wilmington

Globetrotter Retreat too - Minutes to the Mountain

Newly renovated, fully furnished in heart of quaint mountain village; minutes to Mount Snow, Green Mountains & lakes. Year round outdoor activities: snow sports in winter, watersports/hiking in summer. Quiet 1 bedroom apt on 2nd floor sleeps 4 people in comfort. Private balcony overlooks tranquil woods & rolling river. Steps to restaurants, bars & shopping. Supermarket is a short walk. Free Moover bus stop across the street ride for free to local destinations! 18 years or older guests only.

5 out of 5 average rating, 125 reviews

Cabin in Wilmington

Mid-mod VT Dream Chalet near skiing, lake & forest

Surround yourself in nature and cozy modern comfort. The romantic mid-mod-styled chalet backs to 10 acres of peaceful forest yet is just 12 min drive to Mount Snow for great skiing. 3 min. to the boat launch of gorgeous Lake Whitingham where you can rent jetskis & boats or go swimming & fishing. Hike trails to the charming town of Wilmington with its coffee shops & restaurants. Pools & hot tub up the road at clubhouse. Just steps away from iceskating, pickleball, hiking & snowmobile trails.

Guest suite in Wilmington

A spacious great room features a comfortable seating area with a white couch, eclectic armchair, and colorful floor design. Artistic decorations are placed on the walls and shelves, with a kitchenette visible in the background. A piano and drums are positioned nearby for guest use.

4.93 out of 5 average rating, 831 reviews

Architectural GuestSuite

The Guest Suite is located on the first floor of an architectural studio in historic Wilmington, Vermont. Please enjoy the piano, drums, and art supplies! The Guest Suite is both UNIVERSALLY ACCESSIBLE, TOBACCO FREE, and ANIMAL FREE due to allergies in our family. LineSync Architecture staff will be working from 8:30am - 5ish upstairs, and once in a while on the weekends. When guests are in we try to be super sensitive and quiet, but footsteps will be heard!

4.98 out of 5 average rating, 766 reviews

An inviting outdoor space features colorful chairs surrounding a fire pit, set against a winter backdrop. A cozy seating area on a deck showcases modern decor, including a patterned throw and a view of rolling hills framed by an oversized circular window.

Cottage in Shaftsbury

Schoolhouse Spa Retreat on a Vermont Farm

Escape to our historic and lovingly-renovated schoolhouse on a 250-acre verified-regenerative farm, where Green Mountain views meet modern comfort. Unwind in your private hot tub and barrel sauna after exploring farm trails, then fall asleep to the gentle sounds of sheep grazing in the pastures below. This is Vermont at its most authentic—working farm life with all the luxury. Level 2 EV charger, in-unit washer/dryer, and ductless AC for summer comfort.

4.98 out of 5 average rating, 526 reviews

A well-lit kitchen and dining area features a wooden dining table surrounded by six chairs. Light hardwood flooring complements the gray cabinetry. A potted plant sits on the table, and modern appliances are visible in the background, including a refrigerator and stove.

Apartment in Wilmington

**Happy Hour! Gorgeous & Modern Downtown Retreat**

Come enjoy our beautiful apartment above our liquor store in downtown Wilmington! Lots of local shops and dining right in town! We are along a river and next to a hiking trail system! Walking distance to the serene 10+ mile lake; kayaks, stand-up paddle boards or motor boat/jet ski rentals nearby. In the winter, enjoy local trails on snowshoes or cross-country skies; only 15 minutes to Mount Snow! We look forward to meeting you!!!

5 out of 5 average rating, 125 reviews

Chalet in Wilmington

Mt Snow Chalet: Peaceful Escape w/Hot Tub

Escape to the serene beauty of Vermont's Green Mountains at the Mount Snow Chalet, a charming retreat nestled on a private wooded lot in the desirable Chimney Hill community of Wilmington. 🏠🌳 Just minutes from the slopes of Mount Snow, our chalet offers the perfect blend of rustic charm and modern amenities for an unforgettable getaway. Designed with love and care, we invite you to relax and stay awhile! 🥰

4.95 out of 5 average rating, 197 reviews

The bedroom is designed with a spacious bed adorned with crisp white linens. A large triangular window provides a serene view of lush greenery outside, allowing natural light to fill the room.

Cabin in Townshend

Modern Cabin with Outdoor Spa on Vermont Farm

Romantic modern cabin with private hot tub on a 100-acre Vermont farm. This Scandinavian-style retreat features soaring windows, a king bed with luxury linens, a cozy fireplace, and a sleek kitchen. Perfect for couples seeking a peaceful getaway, farm stay, or eco-friendly escape. Soak under the stars, meet our friendly goats, and enjoy the beauty of southern Vermont from your light-filled solar-powered cabin.

Popular amenities for Wilmington outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

4.93 out of 5 average rating, 107 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, 125 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

The Vermont Farmhouse|Hiking|Dog Trails|Village

4.99 out of 5 average rating, 151 reviews

An interior view showcases a modern staircase with wooden steps and a metal railing, leading to a second floor. Natural light floods the space through large glass windows, illuminating the wooden walls and a stone fireplace. A green plant adds a touch of nature.

Home in Londonderry

Modern 3-bedroom A-frame in Londonderry w/ Pond

4.98 out of 5 average rating, 156 reviews

The historic Gate House is framed by lush greenery and a manicured lawn, set against a vibrant sunset sky. Its stone façade and charming architecture are accentuated by soft lighting that bathes the exterior in warmth, inviting guests to explore the expansive outdoor space.

Home in Bennington

The Gate House--Experience Vermont!

4.94 out of 5 average rating, 110 reviews

A cozy living area features a brown sofa and a patterned rug, complemented by side tables and a lighted lamp. An accent chair adds to the seating, while a television is mounted on the wooden wall. Art pieces hang above the fireplace, enhancing the rustic charm.

Home in Dover

Forest Lane - Roomy Mt Snow Home with Hot Tub

4.98 out of 5 average rating, 536 reviews

Home in North Adams

Steps to MoCA private house + SAUNA!

4.98 out of 5 average rating, 425 reviews

A spacious living area features large floor-to-ceiling windows offering a view of the green outdoor space. A plush sofa, accented with colorful cushions, sits in front of a wooden coffee table. A modern dining area is visible in the background, illuminated by soft lighting.

Home in Winhall

Stunning mid-century house on 2.5 private acres

Superhost

A charming treehouse sits elevated on wooden stilts, surrounded by lush greenery. Soft lighting decorates the deck area, creating a warm environment. A gravel path leads to the entrance, while the tranquil pond reflects the evening sky in the background.

Home in South Londonderry

4.84 out of 5 average rating, 183 reviews

Lovers Honey Pond Treehouse with hot tub & sauna

Apartment rentals with outdoor seating

Apartment in Shelburne Falls

The bright studio features a cozy sleeping area with a spacious bed, a comfortable yellow armchair, and two plush couches. A coffee table sits in the center, with large windows allowing natural light and views of greenery. A television is mounted on the wall.

4.97 out of 5 average rating, 640 reviews

In town, newly renovated studio with private deck

4.88 out of 5 average rating, 436 reviews

A serene view from the deck showcases a green meadow leading to a small pond surrounded by grass. Rolling hills can be seen in the distance, framed by trees. A few outdoor chairs are placed near the pond, inviting relaxation in the natural setting.

Apartment in Guilford

Apartment with a view

4.99 out of 5 average rating, 188 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

4.95 out of 5 average rating, 133 reviews

A spacious living area features a comfortable, light-colored sofa with multiple cushions. A low, dark wooden coffee table is centered on a textured rug. Green plants are positioned throughout, and ample natural light enters through large windows adorned with simple treatments.

Apartment in Putney

Minimal organic hideaway inspired by nature

4.95 out of 5 average rating, 189 reviews

A cozy living area features a light grey sofa paired with a wooden coffee table. An accent chair with a textured throw sits beside a basket. A large cow print hangs on the wall, with two framed pieces nearby. A patterned rug covers the floor.

Apartment in Bennington

Cooper's Place

4.86 out of 5 average rating, 112 reviews

A cozy bedroom area features a spacious bed with neatly arranged pillows. A wooden dresser and mirror complement the room, while a small sink is visible beside fresh towels. Soft lighting enhances the warm tones of the wooden accents throughout the space.

Apartment in Dover

*Betimor North Apt.4 Newly renovated Mt. Snow

Apartment in Shelburne Falls

A cozy living room features a brown leather sofa adorned with patterned cushions. A coffee table with decorative items sits in front of the sofa, while a large window allows natural light to illuminate the space. A potted plant and artwork decorate the room, enhancing its charm.

4.95 out of 5 average rating, 148 reviews

River View Apt in Shelburne Falls Historic Village

Apartment in Williamstown

4.94 out of 5 average rating, 351 reviews

COLD SPRING

Condo rentals with outdoor seating

Superhost

Condo in West Dover

4.75 out of 5 average rating, 161 reviews

Beautiful condo 2.5 miles from Mount Snow

A snowy landscape showcases the mountain in the background with ski trails visible. The foreground features a winter scene with snow-covered ground and trees. A building is partially visible on the left, adding to the serene atmosphere.

4.85 out of 5 average rating, 117 reviews

Mount Snow Ski Chalet

A spacious living area features a large sectional sofa adorned with cozy throw pillows, complemented by a textured area rug. Natural light pours in through expansive windows, enhancing the inviting atmosphere. A side table and a plush armchair add to the comfortable seating options.

4.99 out of 5 average rating, 135 reviews

Summer Dream! The Handle Lodge at Snowtree Condos

5 out of 5 average rating, 16 reviews

Walk to Food/Entertainment, 5 Min Drive to Mt Snow

4.95 out of 5 average rating, 120 reviews

The exterior of the condominium building is showcased, featuring three levels with large windows that allow natural light in. A central staircase leads to the entrance, flanked by green grass and small shrubs, creating a welcoming appearance.

Condo in Stratton

Great 2 bedroom condo at Stratton Mountain

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.

4.95 out of 5 average rating, 99 reviews

Great Amenties-Seasons Condo gym-sport 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.

4.91 out of 5 average rating, 67 reviews

Ski Condo 5 Min from Mt Snow

A spacious living area features a large sectional sofa adorned with decorative cushions. A wooden coffee table sits in front, with a lamp beside it. A dining area is visible, accompanied by a window allowing ample natural light and a view of the surrounding trees.