Vacation rentals with outdoor seating in West Windsor

Find and book unique accommodations with outdoor seating on Airbnb

Top-rated accommodations with outdoor seating in West Windsor

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

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Guest favourite

Farm stay in Plainfield

4.97 out of 5 average rating, 176 reviews

Renovated 1817 Hobby Farm Close to Dartmouth

Come stay at our hobby farm in Plainfield Village! Experience country living with a 20-minute proximity to Dartmouth University. It is a daily work in progress, gardening and taking care of the chickens and sheep, so it is not perfect, but it is lively and ever-changing. You can see gorgeous views of Mount Ascutney from your window, hike to the French Ledges, visit St. Gaudens Park, or J.D. Sallingers farm. Every season is beautiful here! Or learn how to make macarons :) if you are brave enough.

Jan. 11 – 18

$234 CAD per night

Guest favourite

Guesthouse in Hartland

4.96 out of 5 average rating, 160 reviews

Cottage for Two/Solo Getaway/Musician's Retreat

Luxurious, well appointed cottage with beautiful sunrise view located between Woodstock VT and Hanover NH. An inspiring treat for musician’s getaway is a fully restored 1929 Steinway L. Full kitchen, custom cabinets, gas fireplace, energy efficient heat pump, washer, dryer and very comfortable queen bed. A romantic getaway in the woods, a place to relax, work in peace, or explore the beauty and history of the area. Hiking, biking, fly fishing, hot air balloon rides and shopping are all close by.

Oct. 30 – Nov. 6

$271 CAD per night

Guest favourite

Cottage in Hartland

4.97 out of 5 average rating, 420 reviews

Breeze Hill Cottage

This cozy two bedroom home sits on a rural dirt road overlooking fields, woods, and the NH mountains. Watch birds from the window, relax on the patio, and enjoy the flower gardens. The cottage boasts modern amenities mixed with antiques. Please note: if we don’t respond to an Airbnb message and you need to speak with us, call us on our phones day or night!!! We have had people message us when we were asleep and so we have not been aware and have not responded. Call us! We will hear the phone!

Apr. 4 – 11

$202 CAD per night

Guest favourite

Guesthouse in Woodstock

4.98 out of 5 average rating, 207 reviews

Cozy Little Spot (Self Check-in)

Contactless check-in. Cozy guest house, cabin-studio-getaway; enjoy the sounds of a stream outside the window (next to the bed). Views of a larger brook below. The"Cabin"is nestled in the trees giving a feeling of floating above the brook below. The interior is decorated w/family heirlooms gathered from around the country. Nothing fancy, just a cozy simple getaway. 3.25 mi from town. Choose from a variety of activities in town or hop on nearby trails. NO PETS ALLOWED. ZERO CONTACT WITH OWNERS.

Feb. 26 – Mar. 5

$252 CAD per night

Guest favourite

Condo in Killington

4.95 out of 5 average rating, 130 reviews

🎿Cozy Fireplace Condo-Mins. to Everything 🚵

Seeking Adventure? This end unit garden level condo is 6 minutes to Killington AND Pico! Quick access to the Appalachian Trail to ATV, mountain bike, hike, and swim. Relaxing? Work remotely with fast Wi-Fi, hang on the porch swing, or unwind in front of the wood fireplace. Hop in the power adjustable king bed, pull the darkening shades, and turn on the sound machine for restful sleep so you can wake up and do it again! A portion of each stay is donated to local VT nonprofits

May 2 – 9

$161 CAD per night

Guest favourite

Tiny homes in Hartland

4.94 out of 5 average rating, 253 reviews

Private Modern Cabin w/View of Fields, Hills

Enjoy a modern private cabin in the heart of Vermont's pastoral Upper Valley Region. Combining "Glamping" with the comforts of a permanent structure, the "HakuBox" (Haku means "to exhale") was designed to sit lightly on the land and offer a simple, restorative experience. Note: no shower, but swimming holes nearby! Queen bed, fire pit w/grill, free firewood, Adirondack chairs, picnic table, free coffee & tea, dog-friendly with cable trolley, food & water bowls. $29 pet fee applies.

Feb. 8 – 15

$207 CAD per night

Guest favourite

Barn in Chester

4.99 out of 5 average rating, 495 reviews

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.

Oct. 18 – 25

$161 CAD per night

Guest favourite

Apartment in Weathersfield

4.99 out of 5 average rating, 157 reviews

The Loft at Weathersfield

Close to Okemo, The Loft at Weathersfield, is just 1/2 hour south of Woodstock / Hanover area and 22 minutes from Okemo Mountain. The Loft, is located in a private agricultural setting with easy access to Vermont's best biking, hiking, fly fishing, skiing, and many equine trails. The loft is 900 square feet with a kitchen/dining room, living room, full bath, one bedroom with a queen bed and one twin bed. There is a spacious deck off the kitchen and a car port underneath.

Mar. 4 – 11

$198 CAD per night

Guest favourite

Cabin in West Windsor

4.98 out of 5 average rating, 206 reviews

Sunset Cabin - your private romantic hideaway

Your private woodlands retreat awaits. Nestled atop a beautiful 10 acre meadow with 25 acres of woods for you to enjoy; this rustic, pet friendly cabin is a perfect romantic hideaway. Two trout ponds are steps from your door for fishing and swimming. Just a few minutes from Mt. Ascutney's hiking and mountain-biking trails and in the middle of fantastic cycling country. WiFi now available! Sunset Cabin is a marvelous spot for enjoying fall foliage and exploring Vermont.

Apr. 27 – May 4

$268 CAD per night

Guest favourite

Guest suite in Brownsville/West Windsor

4.99 out of 5 average rating, 161 reviews

Cozy Guest Suite in Charming Farmhouse

Your two story guest suite is attached to the (main house) with a private FRONT DOOR entry. Sorry there are no cooking elements available. Please take note that the antique stairs to the second floor are steep. You will find your very own first floor library/eating area with WiFi, mini fridge, coffee maker and 1/2 bath. Upstairs is a comfy bedroom suite with a private modern bathroom that includes a shower and Jacuzzi tub. None of these area are shared. It’s all yours!

Jun. 25 – Jul. 2

$253 CAD per night

Guest favourite

Guest suite in Grantham

4.98 out of 5 average rating, 189 reviews

Studio 154, Sunapee/Dartmouth region sleeps 4

Studio 154 is tucked away on a quiet cul-de-sac in a country setting. 18 mins to Lebanon and 25 mins to Mount Sunapee. A short drive through the neighborhood past mountain views, King Blossom Farm Stand, and meadows that frequently host wildlife and sunsets. The studio has 2 queen sized beds, 3/4 bath, love seat, dining table and work desk. Enjoy fast WIFI, 42" tv, USB plugs next to the night stands and tv shelf. Service fee is included in the price!

Oct. 9 – 16

$174 CAD per night

Guest favourite

Condo in Ludlow

4.92 out of 5 average rating, 123 reviews

Okemo Ski-in/Ski-out, Steps to lift Condo

Just steps of walk to the amazing Okemo slopes, C Building is the closest property to the A-Quad/B-Quad lift and this building offers convenient parking right downstairs and free wi-fi (dedicated Xfinity modem, no issue video conference). You’ll love this cozy place with hardwood floor and private balcony and sunshine after skiing. Great sun exposure. Fireplace has been updated to electric fireplace starting from 2023-2024 season.

May 9 – 16

$168 CAD per night