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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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Cabin in Wardsboro

4.87 out of 5 average rating, 104 reviews

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.

Tiny home in Wilmington

4.99 out of 5 average rating, 217 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!

Cabin in Jamaica

5 out of 5 average rating, 217 reviews

New Cabin in Jamaica

Recently constructed 500sq ft passive solar cabin, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

Cabin in Newfane

4.95 out of 5 average rating, 153 reviews

Cozy Cabin in Southern VT

Take it easy at this tranquil getaway. Fall asleep to chirping bugs and wake up to birdcalls. This is a quiet, lovely cabin in Newfane VT. Read a book, walk the meditation circle, swing in the hammock, and explore all that Southern VT has to offer. Close to swimming holes, hikes, country stores, flea and farmers' markets, and ski mountains (Mt Snow and Stratton) Pets and children are welcome, but there is only one queen bed. We can usually provide a travel crib if requested in advance.

Rental unit in Dummerston

4.96 out of 5 average rating, 195 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.

Barn in Marlboro

4.95 out of 5 average rating, 294 reviews

The Studio With a View. Bring your dog, too!

Our stylish Studio, a not so tiny Tiny House, is nestled into the Southern Vermont hillside and surrounded by nature. Enjoy the view from the deck, and cozy up in the newly renovated flower barn with a cup of coffee or tea and a great book. Well-mannered dogs are welcome, they will enjoy the fenced-in area right off the deck. Features: efficiency kitchen and dining area, cozy living space, queen-size bed, and a full bathroom. The large covered porch overlooks fields and trees.

Cottage in Newfane

4.99 out of 5 average rating, 207 reviews

Cozy Vermont Antique Sugar House with Fireplace

Enjoy a peaceful and unique stay at this beautiful 1796 Sugar House. Luxury bedding, cozy fireplace, soaring timbers to a cathedral ceiling make this a special place. There is a Queen size bed on the main floor and twin beds in the sleeping loft accessible by a ladder. Try some of our wonderful local restaurants and shops. Lots of hiking trails to explore. Winter sports all around, or just enjoy some hot chocolate, a fire, and a good book. You are sure to enjoy the “Sugar House”.

Cabin in Newfane

4.98 out of 5 average rating, 258 reviews

Log Cabin: Amazing Views, River Frontage, Hot Tub

Come stay in our sparkling clean, renovated log cabin in the woods with beautiful views of river, mountains and stars. Located by the charming village of Williamsville, close to historic Newfane village, 12 miles from Mount Snow for skiing, and right on the refreshingly cool and clear Rock River. It's the perfect place for a romantic getaway, a family vacation or quality times with dear friends. Recent addition: outdoor hot tub with views of mountains, river and open sky above.

Guest suite in Brattleboro

4.94 out of 5 average rating, 555 reviews

Charming studio in renovated 19th century church.

This spacious studio apartment is located in the former Swedish Congregational Church in historic Swedeville, a secluded hilly neighborhood built by Swedish immigrants in the 1800's. For years it housed Rick and Liza’s stained glass studio, which they have now lovingly and creatively transformed into a residence. The rental is minutes from the interstate and one mile from downtown Brattleboro, but the neighborhood has a rural and somewhat European flavor to it.

Rental unit in Brattleboro

4.95 out of 5 average rating, 165 reviews

Contemporary forest eco-retreat, mountain views

This is an open, light-filled one-Bdm apartment on the lower level of our hillside home, surrounded by forests, with stunning views. Your space is 719 sf + access to laundry. We are fully vaccinated, and ask the same of guests. If you think you may have Covid please tell us. We welcome all kinds of people, regardless of race, ethnicity, gender, etc. We may ask questions before accepting people who don’t have many prior reviews. We don't take pets, sorry.

Cabin in Putney

4.9 out of 5 average rating, 130 reviews

Cabin getaway in Southern Vermont

Let us share our little piece of Vermont with you! Located off a dirt road, tucked into a corner of our working homestead, you'll find a space to relax, unwind, and reconnect. This cabin has everything you need for a private and comfortable escape. Downstairs you’ll find a comfortable leather couch, small kitchen, & bathroom with vanity & shower. The bedroom (located upstairs) has a queen sized bed. All linens provided.

Rental unit in Newfane

4.97 out of 5 average rating, 433 reviews

Rock River Retreat: VT Oasis Pet Friendly

Your private treetop guest suite and beach await at our 1790's colonial on the Rock River in the quiet village of South Newfane, VT. PLEASE READ THE ENTIRE DESCRIPTION BELOW RE: PET POLICIES & kitchenette details. We welcome your furry family members for a $10 fee per pet, per day.

Vacation rentals for every style

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Chalets

Adventure-ready homes with après-ski style

Popular amenities for Windham County outdoor seating rentals

Free parking on premises

Air conditioning

House rentals with outdoor seating

Home in Brattleboro

4.95 out of 5 average rating, 116 reviews

Spacious Brattleboro home on river, walk to town

Home in Brattleboro

4.95 out of 5 average rating, 170 reviews

Frosted Willows

Home in Wardsboro

4.95 out of 5 average rating, 100 reviews

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

Home in Wilmington

4.99 out of 5 average rating, 189 reviews

Vermont Sugar House Retreat

Home in Putney

4.99 out of 5 average rating, 208 reviews

Lovely Brick Schoolhouse

Home in Readsboro

4.86 out of 5 average rating, 124 reviews

December in Peaceful Vermont (Pet Friendly)

Home in West Brattleboro

4.93 out of 5 average rating, 108 reviews

Modern Spacious Home with Mountain Views

Home in Newfane

4.98 out of 5 average rating, 130 reviews

Peaceful cabin close to skiing & Brattleboro

Apartment rentals with outdoor seating

Rental unit in Townshend

4.93 out of 5 average rating, 218 reviews

Private Apt. on Farm, with Hot Tub with views!

Rental unit in Marlboro

4.93 out of 5 average rating, 251 reviews

Shakespeare’s Folly Side Farm and AirBnB.

Rental unit in Wilmington

4.98 out of 5 average rating, 464 reviews

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

Rental unit in Brattleboro

4.9 out of 5 average rating, 351 reviews

Quiet St in Town, gardens, terrace

Rental unit in Guilford

4.88 out of 5 average rating, 395 reviews

Apartment with a view

Rental unit in Londonderry

4.97 out of 5 average rating, 159 reviews

Cozy Apt in Historic Building Near Ski Resorts

Rental unit in Brattleboro

4.98 out of 5 average rating, 121 reviews

River View apartment

Rental unit in Brattleboro

4.89 out of 5 average rating, 538 reviews

Cozy, Private & Great location for exploring VT !

Condo rentals with outdoor seating

Condo in West Dover

4.75 out of 5 average rating, 132 reviews

Beautiful condo 2.5 miles from Mount Snow

Condo in Dover

4.99 out of 5 average rating, 105 reviews

Winter Dream! The Handle Lodge at Snowtree Condos

Condo in Stratton

4.96 out of 5 average rating, 24 reviews

Ski In/Out, Cozy 3BR Condo steps to Village

Condo in Dover

4.95 out of 5 average rating, 37 reviews

Ski in Ski out condo great location

Condo in Dover

4.88 out of 5 average rating, 33 reviews

Ski Condo 5 Min from Mt Snow

Condo in Stratton

5 out of 5 average rating, 29 reviews

Your Vermondo awaits: Steps to Lifts & Village.

Condo in Dover

4.94 out of 5 average rating, 72 reviews

Cozy Mt Snow Ski In / Out

Condo in Dover

4.78 out of 5 average rating, 94 reviews

Cozy Mount Snow 1 Bed : Hot tub, Sauna, Deck

Destinations to explore