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Vacation rentals with outdoor seating in Windham County

Find and book unique outdoor seating rentals on Airbnb

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Popular amenities for Windham County outdoor seating rentals

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

DebbieRating, 5 stars2 months ago
Absolutely incredible place! Tons of room, bathrooms for each bedroom was a big hit. Amazing location. Views were magnificent after 8 inches of snow and some freezing rain. Perfect excuse to not leave the house and enjoy the peaceful serenity over a nice margarita. Fall views must be totally awesome. Don’t need to bring anything except you, your friends and some food. The home has everything you need, all set and ready to go, and I mean everything you’ll need. The house manager Teri was an absolute peach. Her connection to the house and knowledge of the local history was amazing. 5 STARS doesn’t do this place justice. Already planning a return visit.
Guest favorite
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

AnnaRating, 5 stars2 weeks ago
I had a wonderful stay while visiting Brattleboro for work. The house is just lovely and extremely comfortable. The kitchen had everything that we needed. I’m hoping to stay again in the future when working in the area.
Top guest favorite
Home in Wardsboro
4.95 out of 5 average rating, 107 reviews

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

NickRating, 5 stars2 months ago
We truly enjoyed staying here!! The hosts were amazing! They gave us plenty of local recommendations that made our stay so enjoyable. The home was wonderful. Plenty of this to do if you don’t want to leave. Game room was a great bonus!! We can’t wait to return!
Superhost
Home in Windham
4.87 out of 5 average rating, 113 reviews

Magic Creek

DanRating, 5 stars1 month ago
Cute Vermont farmhouse that had everything that you needed. We enjoyed Cooking inn and hanging out in the living with the fireplace. The hot tub was so much fun after a cold day on the mountains. There is a cute little coffee shop and super market only 10 minutes away.
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

TheresaRating, 5 stars1 month ago
Clean and comfortable. Great host who goes above and beyond to make his guests feel comfortable and at home. The beds were comfortable and the bathrooms clean. This place has everything that I look for in an AirBnB stay. We hosted a get together for a dozen family members who live in the area. They were the reason for our trip. People gathered in small groups in the kitchen, living room, dining room and TV room. Plenty of room. It was like having company in my own home.
Guest favorite
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

AveryRating, 5 stars3 weeks ago
This spot is absolutely perfect to be on a quite spot to enjoy nature but still right within walking distance of the center of Wilmington. The cabin itself is beautifully appointed, gorgeous, and super comfortable. Due to rain we ended up spending most of our time inside relaxing and watching movies, and have zero regrets about it. The host was also extremely friendly, helpful and responsive. I'll definitely be coming back again and recommend this for a Wilmington get away weekend!
Superhost
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

CaseyRating, 5 stars2 months ago
Great place. Very isolated and a beautiful location but still has all the creature comforts. The deck, view, and space are amazing. Fast WiFi, 2 bathrooms, and a dishwasher with garbage disposal are really cool in a rustic location like this. The wood fires hot tub was obviously the star of the show. Clear instructions and good communication for everything. The gas grill and gas fire pit were nice. Every thing was comfortable and great. Stress free. Hope to stay here again, thanks for everything.
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, 116 reviews

Modern Spacious Home with Mountain Views

JoannaRating, 5 stars1 month ago
My family of four loved Christine’s place! She is so thoughtful, leaving yummy snacks plus necessities as well. She’s a great baker and provided us with some yummy treats! The beds were super comfy and cozy, bathrooms were clean and well-equipped and we loved being both close to downtown but also could go hiking out the back door. We feel so grateful to have had such a lovely and relaxing place to stay. Thank you, Christine! ❤️

Apartment rentals with outdoor seating

Guest favorite
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**

LisaRating, 5 stars2 weeks ago
Beautiful apartment in the center of Wilmington. We own land and have our camper set up in the next town over, but with the cold weather lately, the camper is still winterized. We wanted to come up and get some yard work done and stay locally, and this apartment was the clear winner! Walking distance to our favorite coffee shop, lots of restaurants, my favorite bookstore (!!) and walking trails. Loved the deck- even though it was April and iffy weather, we were able to have takeout dinner outside one night! So grateful that Jennifer allows pets, as we have two dogs and it’s often hard to find pet friendly Airbnb accommodations that are in a good location and as clean as this place! Jennifer was so kind, accommodating and responsive. She went out of her way to make sure we had a great trip- she’s definitely one of the best hosts we’ve had! Thank you for making this week wonderful! We will be back.
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

KristenRating, 5 stars2 days ago
We loved our stay at Jaki’s place! Very easy check in, easy to find, no issues at all. Very comfortable place and walkable to downtown. Would definitely stay here again!
Guest favorite
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

NateRating, 5 stars6 months ago
Mariann has a great space in a great location. Very accommodating and friendly, made you feel very welcome . Very responsive. Really nice area. Would highly recommend.
Guest favorite
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

C. GavinRating, 5 stars3 weeks ago
The quintessential Vermont Airbnb! Beautiful surroundings, lots of outdoor activities, and easy to get into town with great restaurants. The hosts are very helpful and provide everything needed for a relaxing stay.
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

XianlongRating, 5 stars1 month ago
Thanks for the host making this place like home. Furnitures are well organized. My partner and I love the sofa in the living room. There is a big sofa and single arm chair sofa. It’s good for staying with partner to kiss cuddle and more. We love the well organized kitchen. Very well-equipped. They even have some stock of food, coffee and tea bags just in case if you are hungry in mid night. We came here for skiing trip. It’s just 15 min to Mt Snow, 1.5h to Okemo. Stratton is also around this area. Great location for mountain staycation.
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

AnnaRating, 5 stars3 weeks ago
This property is definitely within the top five Airbnb’s that I’ve ever stayed at! The apartment is absolutely beautiful with no detail missed. The kitchen was impeccable with light snacks provided and coffee/creamer, which is a huge plus for me. The bathroom was spotless with beautiful, plush towels and a lovely washer and dryer set. The living room was very comfortable with a reclining couch. The bed was very comfortable with plush linens. I can’t wait to stay again when I’m working in town.
Guest favorite
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

JoshuaRating, 5 stars1 month ago
This is a lovely home in a beautiful setting. It is quite close to Stratton and the hosts were all great communicators with a quick response time. I hope to stay there again sometime!
Guest favorite
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

William JeffreyRating, 5 stars2 months ago
beds comfortable. heating works well. everything works well.

Condo rentals with outdoor seating

Guest favorite
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.
Condo in Dover
4.83 out of 5 average rating, 108 reviews

Mount Snow Ski Chalet

BarryRating, 5 stars2 months ago
Great place to stay. There are no Ubers the week we stayed there and we should have rented a car. But the place was great.
Guest favorite
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.
Condo in Dover
5 out of 5 average rating, 14 reviews

Slopes N Seasons | Trailside Condo at Mount Snow

AlexanderRating, 5 stars1 month ago
We loved our stay! Everything was immaculate. New. Even ready with some fun board games and a Bluetooth speaker. The location was excellent, and we had a great time! We definitely recommend and would stay again.
Superhost
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.
Condo in Dover
4.92 out of 5 average rating, 12 reviews

Renovated Condo - 5 min walk to Mount Snow

Christoph GRating, 5 stars1 month ago
beautiful condo, well maitained and bathrooms new and remodeled. Great location to the ski lifts. He woks great, walls are solid because we couldn't hear the neighbors and all units were full this weekend. Nice fireplace and wifi worked great for the kids and all big flat screen tv's were excellent. Easy kitchen to cook in for the whole family. Best condo we've stayed at in Mt. Snow. Owners answered all our questions and recommendations
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.
Condo in Dover
4.99 out of 5 average rating, 120 reviews

Winter Dream! The Handle Lodge at Snowtree Condos

MarkRating, 5 stars1 month ago
Our family enjoyed our stay at Rafael's condo. The space was very clean and comfy, and exactly matched the description and photos posted here. The fireplace was a great draw, too. If you're planning on skiing at Mt. Snow, the Moover shuttle bus stop is located right outside of this building, which made for a very convenient and quick way to get to Mt. Snow for my family of 4. We would certainly stay here again in the future.
Guest favorite
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.
Condo in Dover
4.95 out of 5 average rating, 58 reviews

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

DavidRating, 5 stars3 weeks ago
Christine is very easy to work with and very responsive. she answered us back right away before and during our stay. the place is great! very cozy and comfortable. I can't wait to go back to her place next time we're in town!
Guest favorite
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

KatieRating, 5 stars1 month ago
Great place to stay conveniently located by the mountain base! We enjoyed walking into the village after skiing. Very clean and cozy and had everything we needed and more. Dana was very responsive! Hope to come again next year!!
Guest favorite
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

LelahRating, 5 stars1 month ago
We loved staying at this property. The location is excellent for access to the village and the lifts. It is also cute to look out over the ice skating pond. It was clean, had all the kitchen amenities you would need to make food, and had fun ski-oriented decorations. It is also close to the hot tub and lounge area within the main building. It had everything we needed to make out ski weekend comfortable and memorable. Can't wait to stay again!
Superhost
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

LauraRating, 5 stars2 months ago
Great place. I’d definitely stay there again. No complaints about the unit or location. —Fun mountain We got lucky with a powder day! If the beginner slope had been open it would’ve been “Ski in -Ski out” but it wasn’t, so we had a hike to get back to the place. —A skier suggested that I duck under the rope, but I wasn’t familiar with the mountain so I wasn’t comfortable doing that. -It should be mentioned since his unit is @ the Top of the slope and you have to hike it with your gear. I was fine, but it might not be ok for everyone. I guess sometimes you have to break the rules!!🤷🏻‍♀️ I’d recommend Tony’s place!

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