Vacation rentals with outdoor seating in Windsor County

Find and book unique outdoor seating rentals on Airbnb

Top-rated outdoor seating rentals in Windsor County

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

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Superhost

Home in South Londonderry

4.85 out of 5 average rating, 149 reviews

Lovers Honey Pond Treehouse with hot tub & sauna

This NEW and 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 is 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! @bentapplefarm

Top guest favorite

Cabin in Killington

4.98 out of 5 average rating, 105 reviews

Camp Poe: Hot Tub+Game Room+Bar+6acres+Patio

Experience the heart of the Green Mountains on our private 6 acre estate. Camp Poe at Estabrook is newly renovated while still maintaining its original Vermont charm--wide plank floors, farmhouse kitchen, wooden beams and a two story family room w/ a wood burning stove. This 3200 sq ft house is perfect for entertaining with two separate living rooms, bar, game room, 12 foot dining tables (inside AND outside) and hot tub. 13 min to Killington Mtn, 10 to Pico & 4min to the #1 golf course in VT!

Guest favorite

Home in Rutland

4.89 out of 5 average rating, 184 reviews

Killington/Okemo, 7p Hot tub, Mtn.views, Spacious!

Mid week deals! Killington Mnt-20min drive, Lake Bomoseen-20min, Pico Mnt-15min Okemo-30min, Downtown Rutland-5min (bars/dining/shopping) Mnt Top Inn-18min, Hiking-10 min. , Neighborhood pool with tennis courts, basketball courts, playground. Beautiful mountain views, peaceful brook on 1+ acre property. Spacious home with hot tub, AC, firepit, fooseball table, grill, deck, patio, screenroom, 2 kitchens, 2 living rooms, washer/drier, fully stocked kitchens. Very fast wifi/netflix/youtubeTV.

Top guest favorite

Home in Sharon

4.99 out of 5 average rating, 102 reviews

The Willow House: a Modern Vermont Retreat

Just 7 miles (12 minutes ) to the Dartmouth Campus, this newly re-built little house sits beside its own pond on the edge of a sheep pasture. All the comforts of a modern home in 600sqft. Enjoy access to hiking trails and State Forest lands as well as an easy drive to world-class skiing an hour away and all that the Dartmouth College community offers just minutes away. This is the best of pastoral Vermont, with outside living-dining space ( south facing deck and north facing screen porch).

Top guest favorite

Yurt in Randolph

5 out of 5 average rating, 129 reviews

Howling Wolf Farm Yurt--A Magical Glamping Retreat

Our 88-acre farm spreads up a steep hillside above the village of Randolph, one mile away. The land is a mixture of open areas where we rotate our sheep flock daily, and wooded land with trails and old stone walls. You might hear the occasional car or truck on a nearby road, but more likely you'll hear our sheep baaing to one another or the cows across the valley trumpeting, or the abundance of birdsong. The energy here is calming and peaceful--we know you will love it as much as we do.

Top guest favorite

Cabin in Stockbridge

4.95 out of 5 average rating, 107 reviews

1958 Classic "Hunting Cabin" w/ Breathtaking Views

Welcome to CAMP TREETOPS, located in the heart of the beautiful Vermont mountains. Our cabin is nestled at the top of a private mountain, surrounded by breathtaking views of Killington, Pico mountains, and the White River. Originally purchased from a Sears & Roebuck catalog as a hunting cabin owned by the same family until 2019. The cabin has since been transformed into its original vintage classic camp décor with antique furnishings and unique vintage finds that take you back in time.

Superhost

Cabin in Bridgewater

4.91 out of 5 average rating, 100 reviews

100 Acres Views & Creek near Woodstock/Killington

You will leave the demands of your busy lifestyle behind when you vacation on our 100+ acre 4 BR 2 BA cabin property with a babbling crystal clear mountain creek. Place your beach chair in the creek, relax with your favorite book for Best Spa Experience Ever! Large open covered porch with porch swing seating to enjoy the expansive mountain views, listen to the leaves rustle and the stream running in the distance. Miles of hiking & biking trails, skiing, restaurants and more nearby.

Superhost

Cabin in Killington

4.88 out of 5 average rating, 109 reviews

Killington Cabin: Big Home. Sleeps 20. Hot Tub!

Killington Cabin: an enchanting wood-beam haven in Vermont's Green Mountains. Ideal for every season—ski, bike, hike or unwind. Our duplex offers 8 bedrooms, 4 baths, 2 kitchens, 2 living spaces, and decks w/ hot tub & grills. Located just off the main Killington Road, reach the resort in 5 minutes while relishing the tranquility of our private road. Comes with smart TVs, high-speed WiFi, streaming, and Alexa. Hot tub fee applies mid-Mar to mid-Dec & pet fee may apply. More below.

Top guest favorite

Tiny home in Hartland

4.96 out of 5 average rating, 186 reviews

Cabin on the Hill

Enjoy a stay in the hills of Vermont - glamping at its finest! A 5-10 minute hike UPhill to a secluded getaway in the heart of Vermont. Amenities include a quaint outhouse, a unique outdoor shower, a 2 burner outdoor gas stovetop and a fire pit to roast marshmallows. The 12x14 screened in cabin with ladder accessed loft sleeps 2 comfortably. Don't worry about bringing pots and pans - cabin is equipped with dishes and a water supply. Adjustable LED lights to light up the night.

Top guest favorite

Home in West Windsor

4.97 out of 5 average rating, 117 reviews

Birdie's Nest Guesthouse

Welcome to our newly renovated studio apartment, nestled among the trees in the serene hills of West Windsor, Vermont. Elevated on the second floor, this separate structure offers a tranquil escape with breathtaking views of Mount Ascutney and our own private pond. Immerse yourself in the comforts of this thoughtfully designed studio apartment, surrounded by the natural beauty of the Vermont landscape. Every detail has been curated to ensure your utmost comfort and enjoyment.

Guest favorite

Chalet in Royalton

4.93 out of 5 average rating, 169 reviews

Scandinavian design Chalet w/ private hiking trail

* NEW FROM 8 of NOVEMBER '24: a Goodland Wood Burning Hot tub*. This bright, well-designed Scandinavian-style chalet is the perfect cozy retreat. Nestled in the woods on a plot of 20+ acres, it offers scenic views and a private hiking trail leading to beautiful vistas, transforming into a winter wonderland for skiing adventures, a summer paradise for outdoor relaxation, and a vibrant canvas for leaf peeping during Vermont's stunning fall foliage season.

Guest favorite

Campsite in Vershire

4.88 out of 5 average rating, 172 reviews

Camping on a Private Pond

Picturesque setting on a small pond and a brook for fishing. A bit off the beaten path, yet three miles to the closest store. (There is NO wi-fi or cell service on the pond but you may come up to the house if necessary). We have local hiking and two large lakes close by. Farmer's markets and acclaimed theatre are available throughout the Fall along with local beer-fests. Most of all, we have one of the most stunning foliage seasons in the country!

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What guests are saying

Downhill Haus, 7 beds, between Okemo & Killington

4.91 out of 5 average rating, 55 reviews1 month ago

Great stay near Killington Ski Resort—just a short drive to the slopes! The home was clean, cozy, and well-equipped, with a fireplace that made for the perfect evening spot. Check-in was easy, and the hosts were super responsive. Daniel was very friendly and responsive! Would definitely stay again!

Cabin in Plymouth

What guests are saying

Stunning Artist Retreat Cabin

4.91 out of 5 average rating, 43 reviews1 month ago

We stayed for one night between ski days and had a fantastic time! This cabin was the perfect spot for a peaceful evening. Elizabeth was a wonderful host, meeting us out front and helping with our bags. The cabin was cozy and stayed plenty warm, even on a 0-degree night. We used the toaster oven for dinner, and it worked well. The setting was stunning, especially with the snowfall. The large cabin windows provided beautiful views. I would definitely stay here again. A couple of small areas for improvement: the WiFi wasn’t working and some dishes weren’t fully clean. Overall, a wonderful stay. I’d highly recommend it.

Cabin in Stockbridge

What guests are saying

Okemo Hot Tub Fireplace Billiard

4.93 out of 5 average rating, 67 reviews1 month ago

Our stay was awesome! The driveway was icy but the hosts provided salt for us to use and the snow-pile guy came during our week and spread sand which was very helpful. The house was huge and provided lots of activities and room for everyone to spread out. We had some amazing family dinners using the well equipped kitchen and large dining space.

Chalet in Mount Holly

What guests are saying

Sunset Cabin - your private romantic hideaway

4.97 out of 5 average rating, 242 reviews6 months ago

We *LOVED* our time in the Cabin in the Woods. Sondra and Daniel were very responsive in responding to questions about the property. The layout of the cabin was sensible and comfortable and the bed was very comfortable. We would love to go back! The cabin location is perfect and is sweet and romantic. Sondra and Daniel have thought through every detail. Thanks again for a splendid vacation spot!

Cabin in West Windsor

What guests are saying

The Brook House

5 out of 5 average rating, 27 reviews2 months ago

We really loved our stay! Jeff’s house is convenient to both Woodstock and Quechee. We enjoyed restaurants, hiking and cross country skiing. The house has lovely amenities, including a well-stocked kitchen, comfortable beds and an outdoor fire pit that was cosy to sit around even on chilly February evenings. We would definitely stay again if returning to the area. Additionally, Jeff was super responsive and checked in upon our arrival day to confirm that we had all that we needed.

Home in Hartland

What guests are saying

A quiet x in VT to Ski, Hike, Hot tub~3m Quechee

4.92 out of 5 average rating, 12 reviews2 months ago

I visited Thatcher and Lisa's place for a few days in February with 5 friends. It was an incredible experience overall. The home was a perfect peaceful getaway, with awesome amenities like multiple private rooms, a well-stocked kitchen, hot tub, and games. It is also very nicely located, providing a peaceful rural setting while also having great access to nearby areas like Woodstock, Hanover, and Killington (where we spent ~3 days skiing). Additionally, Lisa and Thatcher really went above and beyond as hosts. They left very clear instructions and recommendations, made sure that we arrived smoothly in the face of inclement weather, and even shipped home an item we left behind. I definitely recommend staying here for your next Vermont adventure!

Home in Hartland

What guests are saying

Chuck's Place

4.93 out of 5 average rating, 43 reviews1 month ago

We rented Chuck’s Place for 8 weeks to use as a ski house for this winter. This house is located 35 minutes from Okemo, 45 minutes from Sunapee and 25 minutes from the Woodstock Nordic Center. It has everything you need including a well-stocked kitchen and two bathrooms. It is actually nicer than the pictures show as they have done some renovations. We especially enjoyed relaxing in the living room after a long day of skiing and watching the sun set on Mount Ascutney. Access to a garage was a major plus for the winter! We also loved being able to use the gas grill the whole time. Ed and Jennifer live nearby and responded promptly if any issues arose. We can’t say enough great things about this place. We felt right at home and are going to miss that view!

Home in West Windsor

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