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Vacation rentals with outdoor seating in Windham County

Find and book unique outdoor seating rentals on Airbnb

Top-rated outdoor seating rentals in Windham County

Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

A cozy chalet is set on a lush green landscape, surrounded by towering trees. The two-level structure features a prominent balcony and a welcoming entrance, with a gentle slope leading toward the house. A grill is positioned on the lawn, ready for outdoor cooking.

Chalet in Stratton

4.99 out of 5 average rating, 167 reviews

Chalet w/Disc Golf & AC near hike/bike/golf/swim

Cozy chalet awaits your stay. This home sits on just under 4 acres. Sit back and enjoy the heated sunroom and stare out at the woods that surround you. You may be lucky enough to spot one of the moose or bear that visit the property. Kitchen remodeled June 2023! Open floor plan w/wood burning fireplace. Main bedroom has Qn bed & twin bunks. Finished basement with new Qn size bed and twin bunk above. Kid friendly home! Mins to Stratton Mtn & Mt Snow for skiing & golf! Free Disc golf on property!

Home in Wilmington

4.88 out of 5 average rating, 105 reviews

MtSnow * HotTub * Pool * Air Hockey * PingPong * Darts

Welcome to our ❄newly listed❄lodge style home! HOT TUB✅ Our home is located on private 2.6 acre lot with beautiful views of Mount Snow in the distance. Our home offers easy access to night life/restaurants and much more. Whether you are skiing, hiking, biking, kayaking or just enjoying the fresh Vermont air, you'll love the comfort of our home. Enjoy a space that is truly convenient, comfortable, child-friendly and fun for you to enjoy during your hard-earned vacation time in southern Vermont!

Home in South Londonderry

4.86 out of 5 average rating, 152 reviews

Lovers Honey Pond Treehouse with hot tub & sauna

Guest Favorite VERY romantic abode…The Honey Pond Treehouse is made especially for you and yours! It’s constructed of all natural materials, has breathtaking views, and outfitted with absolutely everything you need! Lifted high over a stocked trout pond way up in the birch trees…You will enjoy private hot tubbing, sauna time, swimming & hammock time. Skylight was designed for stargazing in bed!! Just minutes to the slopes or enjoy our own groomed trails for Xcountry & snowshoes & nature walks!!

A cozy fire pit is surrounded by stone, situated in the foreground of a spacious lawn. In the background, a modern chalet features large windows and a combination of wood and stone siding, framed by colorful autumn foliage.

Home in Winhall

4.95 out of 5 average rating, 137 reviews

Summit View Ski and Golf Retreat w/hot tub & Sauna

Summit View Chalet @ Stratton is the ideal VT retreat, Minutes from Manchester, directly across the entrance from Stratton's 27 Hole Championship Golf Course. Beautifully remodeled! Relax in the hot tub on the deck with direct summit views in any season. Enjoy shuttle access to lifts, minutes from snowmobiling, hiking, fine dining and shopping. Comfortable accommodations for 6 adults and 5 children. Perfect for 2 families to enjoy any season in Southern Vermont's beautiful Green Mountains!

A charming cottage is nestled in a snowy landscape, surrounded by evergreen trees. The red exterior contrasts with the white snow. A stone chimney rises from the roof, and a small garden area is visible in the foreground, adding interest to the serene winter scene.

Cottage in Chester

4.91 out of 5 average rating, 162 reviews

Green Mountain Country Cottage

Four bedroom cottage centrally located within less than 35 min. of 4 ski resorts, and next to the former Tater Hill golf club. Access to snowmobile trail on site, X-country skiing, hiking, fishing, shopping, restaurants, state parks nearby. In summer and fall mushroom foraging is very productive. For history buffs there is a revolutionary war era cemetery next to the property. Sleeps 10 to 12. The cottage is only available to family groups or responsible adults over 25. NO PARTYING ALLOWED.

Home in Wilmington

4.96 out of 5 average rating, 114 reviews

Family Downtwn Retreat Wilmington-HotTub Firepit

Welcome to our family-friendly home in Wilmington, Vermont! Perfect for group getaways. Our home offers a blend of comfort and convenience. Just a short walk from Wilmington's charming downtown, with easy access to restaurants, shops, and groceries. Mount Snow is only a 12-minutes away, making this an ideal base for both winter skiing adventures and summer hikes. Whether you're here for outdoor fun or cozy nights by the fire pit, our home is ready to make your Vermont getaway unforgettable!

A cozy bedroom is presented with a spacious bed adorned with a white quilt and decorative pillows. A large window offers a serene view of Sadawga Lake, complemented by a window seat nearby. Light wooden cabinetry and overhead lights add warmth to the setting.

Tiny home in Whitingham

4.91 out of 5 average rating, 100 reviews

Cozy Lakeside Tiny Home, Near Skiing

Hot Breakfast and Lunch INCLUDED every day in your stay. Our general store, located 5 minutes away, will make you fresh egg sandwiches, pastries, and coffee. For lunch, come in and get fresh made subs or our famous brick oven pizza slices. A perfect getaway for couples, friends, or family in every season. Enjoy kayaking, fishing, ice skating and boating on serene Sadawga Lake. It's a quick drive to skiing at Mount Snow, shopping and dining in Wilmington, and direct access to the VAST trail.

Top guest favorite

A wooden deck features two black metal chairs and a small table, surrounded by autumn foliage. Sunlight filters through the trees, creating a warm ambiance. Potted flowers in hues of yellow and orange are placed on the deck, enhancing the outdoor setting.

Tiny home in Wilmington

4.99 out of 5 average rating, 267 reviews

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!

A comfortable white sofa with decorative pillows is positioned against a light wall. A small, light-colored side table holds a potted plant. Natural light streams in through a nearby window, illuminating the wooden floor and a blue woven rug beneath.

Apartment in Dummerston

4.96 out of 5 average rating, 221 reviews

HeART Barn Retreat

Peaceful, romantic retreat in this stunningly large and magical barn. This 1850's historic remodeled barn apartment is nestled into hundrends of acres of Nature Conservency. Many old maple and pine trees, hiking trails and breathtaking views will welcome you along the the drive here. If you'd like to book a healing retreat I offer Reiki sessions to guests. Inquire when you book. *Mount Snow is 35 minutes away. Okemo, Stratton, Bromley and Magic is 1 hour away and Stratton is 1 hour away.

Top guest favorite

A rustic wooden cabin is set against a backdrop of lush green mountains, featuring a spacious deck with comfortable outdoor seating. Large glass doors provide a view of the interior, while trees and foliage create a natural privacy barrier.

Cottage in Londonderry

4.96 out of 5 average rating, 217 reviews

Vermont Treehouse - Romantic Private Elegant

3 night minimum, unless prior approval, self checkin. Work remotely. This romantic, elegant, private getaway for two (or one) in our "Treehouse" with sleeping loft, full kitchen & bathroom, screened porch, deck, sauna, WiFi, BBQ grill, etc. Overlooking pasture & mountains. Enjoy the property with 3 miles hiking/snowshoe trails. Guest house on 160 acre private horse farm. Lots to do at nearby ski areas, shopping, hiking, biking, theater in summer. Or just relax. Discount for longer stays.

An inviting interior space features a cozy seating area with a dark couch and a glass coffee table. Natural light enters from a door leading outside, and a wood stove is prominently positioned next to a dining table, enhancing the rustic feel of the camper.

Camper/RV in Guilford

4.92 out of 5 average rating, 132 reviews

Monadnock Sunrise Forest Hideaway

Enjoy a converted camper as your private getaway in Southern VT. Less than 10 min to downtown Brattleboro, yet nestled in the woods for a quiet retreat. Full galley kitchen and living/lounge area. Wood stove for primary heating (electric backup for not so cold days). Outdoor spaces include a fire pit, deck, pool table, hot outdoor shower, outhouse (composting toilet), and forest for galavanting. The place is a perfect fit for up to two adults and one kid (63" long fold down couch).

Top guest favorite

A hammock is suspended between trees, surrounded by lush green foliage. Elevated wooden decks are visible in the background, offering a serene spot to relax and connect with nature. Sunlight filters through the leaves, creating a peaceful atmosphere.

Treehouse in Guilford

4.99 out of 5 average rating, 138 reviews

Cozy tent in the trees on organic flower farm

Tuck yourself into a mature oak forest on the field’s edge of our flower farm, Tapalou Guilds. All-weather canvas tent is pitched with a comfy king mattress inside. Three elevated decks with chairs and a hammock give you options for relaxing and steeping in the forest vibe. Fully equipped outdoor kitchen with propane gas range. We provide potable water from our well. Outdoor shower with on-demand hot water. Simple outhouse with sawdust composting system is clean and convenient.

Vacation rentals for every style

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Cabins

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Apartments

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Houses

A space thats all yours, with room for everyone

Popular amenities for Windham County outdoor seating rentals

Free parking on premises

Air conditioning

House rentals with outdoor seating

Top guest favorite

A spacious deck extends from the house, equipped with an umbrella and several chairs, providing a view of the encompassing greenery and mountains. The home's exterior features warm brown siding and solar panels on the roof, set against a bright blue sky.

Home in Brattleboro

4.94 out of 5 average rating, 121 reviews

Spacious Brattleboro home on river, walk to town

The open dining area features a wooden table surrounded by six light-colored chairs. A view into the kitchen reveals modern appliances and cabinetry. Warm wood accents provide contrast against the light walls, while natural light enters through nearby windows, enhancing the inviting ambiance.

Home in Brattleboro

4.94 out of 5 average rating, 203 reviews

Frosted Willows

Top guest favorite

Home in Wardsboro

4.95 out of 5 average rating, 107 reviews

Hot Tub & Game Room - Ski Mt. Snow/Stratton

Home in Windham

4.87 out of 5 average rating, 113 reviews

Magic Creek

Top guest favorite

A white fireplace with a rustic brick surround serves as a central feature. Above, a shelf displays decorative bowls and books, while soft sunlight casts shadows across the surface. A lamp with a patterned shade stands nearby, adding a touch of warmth to the space.

Home in West Brattleboro

4.88 out of 5 average rating, 152 reviews

Cozy Home for 2-5 People in Vermont

An A-frame chalet is showcased, featuring a gray exterior with a vibrant turquoise door. A front porch is visible, accompanied by stairs leading up. Surrounding greenery and trees provide a natural backdrop, enhancing the inviting appearance of the home.

Home in Wilmington

4.9 out of 5 average rating, 220 reviews

Wilmington A-Frame- Cozy and Convenient

A modern home nestled among lush greenery, standing amidst tall trees with a deck overlooking a river. The building's exterior features large windows and a welcoming appearance, seamlessly integrated into the natural surroundings.

Home in Jamaica

4.94 out of 5 average rating, 173 reviews

Cozy Riverfront Home in beautiful Jamaica

Top guest favorite

A spacious living room features a vaulted ceiling and an arched window that allows natural light to flood the space. Comfortable seating arrangements include two red sofas and a patterned area rug. Shelving units display decorative items, while a media system is positioned above the fireplace.

Home in West Brattleboro

4.93 out of 5 average rating, 117 reviews

Modern Spacious Home with Mountain Views

Apartment rentals with outdoor seating

A serene outdoor area features two hammocks suspended between trees, surrounded by lush greenery. The scene is framed by a stone walkway leading to the riverbank, creating a peaceful setting for relaxation by the water.

Apartment in Wilmington

4.98 out of 5 average rating, 482 reviews

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

Top guest favorite

An open concept living area is highlighted by a comfortable light-colored sofa with decorative pillows. A dark wood coffee table centers the space, while a well-equipped kitchen features modern appliances and a light-colored island with seating. Natural light filters through the window, enhancing the inviting atmosphere.

Apartment in Brattleboro

4.9 out of 5 average rating, 361 reviews

Quiet St in Town, gardens, terrace

The property entrance is framed by natural stone pillars, welcoming visitors to a spacious house set amidst vibrant autumn foliage. A gravel driveway leads towards the home, surrounded by trees displaying rich fall colors under a clear blue sky.

Apartment in Wilmington

4.93 out of 5 average rating, 180 reviews

Quaint cozy vermont apartment

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

4.88 out of 5 average rating, 406 reviews

Apartment with a view

Top guest favorite

A private balcony features a small white table and two matching chairs. A decorative orange vase sits atop the table. Surrounding vegetation includes lush green leaves and a prominent white birch tree, providing a serene view of the tranquil woods beyond.

Apartment in Wilmington

4.91 out of 5 average rating, 134 reviews

Globetrotter Retreat too - Minutes to the Mountain

Top guest favorite

Two white lounge chairs are positioned around a small black fire pit in a grassy area. Lush greenery and trees define the backdrop, while an open space creates a sense of privacy and tranquility.

Apartment in Brattleboro

4.98 out of 5 average rating, 132 reviews

River View apartment

A patio area is visible in front of the wooden structure, featuring a set of chairs and a table. A hot tub is positioned nearby, surrounded by greenery. The entrance to the building is framed by large glass doors, creating an inviting outdoor space.

Apartment in Londonderry

4.96 out of 5 average rating, 580 reviews

Vermont Getaway Apartment

A cozy hallway leads to a sitting area with large windows showcasing stained glass designs. Soft natural light fills the room, illuminating a comfortable seating arrangement including a sofa and armchairs. A warm lamp provides additional lighting, creating a welcoming space.

Apartment in Town of Rockingham

4.9 out of 5 average rating, 100 reviews

Victorian Inn Apartment

Condo rentals with outdoor seating

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.

4.83 out of 5 average rating, 108 reviews

Mount Snow Ski Chalet

A spacious dining area features a long wooden table that seats eight, complemented by modern light fixtures. Large windows allow natural light to fill the room, while a sliding glass door offers access to a private outdoor space. A console cabinet is visible against the wall.

5 out of 5 average rating, 14 reviews

Slopes N Seasons | Trailside Condo at Mount Snow

A private deck is shown, furnished with two blue chairs placed beside a wooden railing. The view includes a serene landscape of trees and patchy snow, indicative of the changing seasons.

4.92 out of 5 average rating, 12 reviews

Renovated Condo - 5 min walk to Mount Snow

Top guest favorite

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, 120 reviews

Winter Dream! The Handle Lodge at Snowtree Condos

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, 58 reviews

Condo w/ great amenities 4-seasons! Ski in Ski out

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

4.94 out of 5 average rating, 103 reviews

Great 2 bedroom condo at Stratton Mountain

A living area features a gas fireplace beneath a mounted flat-screen TV. A comfortable sofa and love seat are arranged around a dark ottoman. Natural light filters through the large windows, partially covered by patterned shades, offering views of the balcony and outdoor scenery.

Condo in Stratton

4.98 out of 5 average rating, 46 reviews

A Village location, Steps to the Lifts & Village

The exterior entrance features a set of wooden stairs leading up to a blue front door, surrounded by stone walls and greenery. The building’s white siding and pitched roof are visible against a cloudy sky.

Condo in Londonderry

4.93 out of 5 average rating, 29 reviews

Magic Mountain Trailside Condo Ski In / Ski Out

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