
Holiday rentals with outdoor seating in Windham County
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Windham County
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

Stone Fence Cabin
Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery & hiking right outside your front door. The Cabin has an open floor plan with a full bath, galley kitchen & dining/living area with pullout futon couch that converts into a 2nd bed. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

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!

Treehouse Haven in Putney-All Seasons
Peaceful, private & fully equipped four-season treehouse, surrounded by nature. ☽ Private & secluded ☽ Central to activities & necessities ☽ Firepit, pellet stove, deck, grill & fully stocked kitchen ☽ Scrupulously clean, unscented products ☽ Clean composting toilet ☽ Tea & local coffee ☽ Hot outdoor shower ☽ 45min to ski resorts ☽ Swimming holes & hikes ☽ WiFi & electricity Visit for romance, time with the family, a retreat from the business of life, or even a remote work sanctuary.

Bright and Modern Chestnut Street Apartment
Enjoy a unique stay at this central, beautifully-remodeled apartment in quaint Brattleboro, Vermont. The apartment is attached to the back of the charming 1914 home where I live, and has a private, separate entrance so guests can come or go as they please. This carefully-curated apartment includes tasteful decor, a well-appointed kitchenette, organic cotton sheets, and natural bath products. Just off Hwy 91, the apartment is located in the quiet, historic neighborhood of Esteyville.

Inviting studio apartment above barn in Vermont
This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. We are as close or as far away as you would like us to be with our house right next door.

Serene Retreat in Nature w/ Woodfired Tub
A romantic and private getaway on a peaceful six-acre farm with views of fields and forest. ☽ Featured in STAY; Gorgeous Cabins of the East Coast ☽ Outdoor wood-fired hottub, surrounded by nature (tub when below freezing) ☽ Elevated design; thoughtful lighting; deeply romantic ☽ Quiet & private; star-studded skies ☽ Woodstove, deck, reading nook, firepit ☽ Local's Area Guide with our favorite spots ☽ Strong wifi, no TV ☽ Scrupulously clean using unscented products

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.

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!

LUXE Forest Retreat
Here you will experience a full sensory immersion in nature while simultaneously enjoying all the comforts of a custom built luxury home. The SY House derives its name from the Japanese expression Shinrin-yoku, which directly translates to "forest bathing... A practice of therapeutic relaxation where one spends time in a forest or natural atmosphere, focusing on sensory engagement to connect with nature." The essence of this house is nature.

Log Cabin: Amazing Views, River Frontage, Hot Tub
A sparkling clean, recently renovated log cabin in the woods with beautiful views of river and mountains. Located by the charming villages of Williamsville and Newfane, 12 miles from Mount Snow, and right on the crystal clear Rock River. It's the perfect place for a romantic getaway, a family vacation and quality times with good friends. Now also with outdoor hot tub with views of mountains, river and the wide, open sky above.

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.

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 Windham County outdoor seating rentals
Holiday House Rentals with Outdoor Seating

The Architect's Cabin, on 10 Secluded Acres

Clark Farm-2 Master-Suites, Great kitchen, views!

Clean, Captivating VT Farmhouse near Stratton!

Large home in scenic Marlboro

Wilmington A-Frame- Cozy and Convenient

Modern Spacious Home with Mountain Views

Peaceful cabin close to skiing & Brattleboro

Governer's Brook Camp - 2 Bedroom
Apartment rentals with outdoor seating

Private Apt. on Farm, Hot Tub with views!

Shakespeare’s Folly Side Farm and AirBnB.

Quiet St in Town, gardens, terrace

HeART Barn Retreat

Apartment with a view

Contemporary forest eco-retreat, mountain views

River View apartment

Minimal organic hideaway inspired by nature
Condo rentals with outdoor seating

Mount Snow Ski Chalet

Winter Dream! The Handle Lodge at Snowtree Condos

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

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

Great 2 bedroom condo at Stratton Mountain

Ski Condo 5 Min from Mt Snow

Cozy Mt Snow Ski In / Out

Cozy Mount Snow 1 Bed : Hot tub, Sauna, Deck
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- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Jiminy Peak Mountain Resort
- Monadnock State Park
- Berkshire East Mountain Resort
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- Stratton Mountain Resort
- Mount Sugarloaf State Reservation
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- Bousquet Mountain Ski Area
- Hildene, The Lincoln Family Home
- Dorset Field Club
- The Shattuck Golf Club
- National Museum of Racing and Hall of Fame
- Peebles Island State Park
- Hooper Golf Course
- Crotched Mountain Ski and Ride
- Northern Cross Vineyard
- Hancock Shaker Village
- Brattleboro Ski Hill
- Bromley Mountain Ski Resort
- Things to do Windham County
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- Nature and outdoors Vermont
- Food and drink Vermont
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