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Vacation rentals with outdoor seating in Wilmington

Find and book unique outdoor seating rentals on Airbnb

Top-rated outdoor seating rentals in Wilmington

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

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Home in Readsboro

4.86 out of 5 average rating, 124 reviews

December in Peaceful Vermont (Pet Friendly)

Beautiful Country Home, nestled in Vermont's Green mountains, panoramic views, with good access by the road. A babbling brook to lull you asleep from the master bedroom, and a clawfoot soaking tub, fully stocked house. Hiking, antiques, shops, lakes, picnics, covered bridges, cozy local inns, mountain views! Enjoy Vermont! Scenic roads, Mt. Snow, VAST trails, Mt.Greylock, Mass MOCA museum, nearby N.Adams, MA, Berkshires. Bennington Wilmington & Mt. Snow. PEACEFUL & PERFECT Vermont getaway! ☺

Home in Wilmington

4.99 out of 5 average rating, 188 reviews

Vermont Sugar House Retreat

Stay at this unique rustic Vermont getaway. Nestled on a quiet hill in Wilmington, this private retreat will serve as the perfect home base for your Vermont adventures. You'll have the house to yourself without a neighbor in sight. While very private and surrounded by beautiful forest, this house is still only a short 5 minute drive from downtown Wilmington. The house is built around an enormous one-of-a-kind natural stone fireplace that was formed atop the old foundations of a sugar house.

Home in Wilmington

4.96 out of 5 average rating, 106 reviews

Family SKI Retreat inWilmington-Walk 2Town-Hot Tub

Welcome to our family-friendly home in Wilmington, Vermont! Perfect for group getaways. Our home offers a blend of comfort and convenience. Just a short walk from Wilmington's charming downtown, with easy access to restaurants, shops, and groceries. Mount Snow is only a 12-minutes away, making this an ideal base for both winter skiing adventures and summer hikes. Whether you're here for outdoor fun or cozy nights by the fire pit, our home is ready to make your Vermont getaway unforgettable!

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.

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.

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.

Cottage in Monroe

4.9 out of 5 average rating, 109 reviews

Pumpkin Pine Cottage: your next adventure awaits!

Explore the Deerfield River Valley and Hoosac Range from this tranquil base. Close to skiing, snow tubing, snowshoeing, hiking, birding, kayaking, white-water rafting, fly fishing, zip lines, and more. Like bikes? Amazing gravel, road, and MTB offerings await. Seek culture? Mass MOCA, Clark Art Institute, Northampton, Shelburne Falls, and the Berkshires are a short drive away. Covered bridges, farm stands, sugar shacks, and waterfalls are too plentiful to count!

Guest suite in Wilmington

4.92 out of 5 average rating, 752 reviews

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!

Rental unit in Bennington

4.93 out of 5 average rating, 620 reviews

The Octopus's Garden

Welcome to the Octopus' Garden, a warm and cozy oasis located in the heart of Bennington, VT. This relaxing one bedroom suite, infused with amenities and much love, comfortably accommodates 2 people. This peaceful space is only a 10 minute walk to art, shops and dining and is the perfect hub for a variety of activities in Southern Vermont and Western Massachusetts.

Cabin in Wilmington

4.93 out of 5 average rating, 441 reviews

Picturesque Cabin near Mt Snow

Enjoy fall in Vermont! Our cabin is the perfect spot to experience cozy VT charm without missing out on modern amenities. The beautiful Green Mountains are right outside our door as well as nearby lakes and rivers. The cabin is well equipped with 3 bedrooms, 1 bath; and you'll love the screened-in porch out back. We’re also dog-friendly!

Vacation rentals for every style

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Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space thats all yours, with room for everyone

Popular amenities for Wilmington outdoor seating rentals

Free parking on premises

Air conditioning

House rentals with outdoor seating

Home in Colrain

4.93 out of 5 average rating, 167 reviews

Secluded Farmhouse Retreat - stunning views

Home in Wilmington

4.88 out of 5 average rating, 163 reviews

Adams Farm-"The Little Farmhouse"

Home in Wardsboro

4.95 out of 5 average rating, 100 reviews

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

Home in Bennington

4.99 out of 5 average rating, 124 reviews

The Gate House--Experience Vermont!

Home in Putney

4.95 out of 5 average rating, 327 reviews

Cozy Train Depot in Putney Vermont

Home in Shaftsbury

4.87 out of 5 average rating, 134 reviews

Cheerful 1 bedroom cottage

Home in New Lebanon

4.99 out of 5 average rating, 362 reviews

The old sawmill from 1771

Home in Guilford

4.92 out of 5 average rating, 196 reviews

Peaceful Country Home

Apartment rentals with outdoor seating

Rental unit in Plainfield

4.97 out of 5 average rating, 259 reviews

Sunny, light filled loft in 1873 Colonial

Rental unit in Shelburne Falls

4.97 out of 5 average rating, 523 reviews

In town, newly renovated studio with private deck

Rental unit in Marlboro

4.93 out of 5 average rating, 251 reviews

Shakespeare’s Folly Side Farm and AirBnB.

Rental unit in Wilmington

4.93 out of 5 average rating, 181 reviews

Quaint cozy vermont apartment

Rental unit in Guilford

4.88 out of 5 average rating, 395 reviews

Apartment with a view

Rental unit in Brattleboro

4.95 out of 5 average rating, 165 reviews

Contemporary forest eco-retreat, mountain views

Rental unit in Brattleboro

4.98 out of 5 average rating, 121 reviews

River View apartment

Rental unit in Newfane

4.97 out of 5 average rating, 433 reviews

Rock River Retreat: VT Oasis Pet Friendly

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 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 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

Condo in Hancock

4.85 out of 5 average rating, 142 reviews

Cozy Condo @ Jiminy Peak

Condo in Dover

4.92 out of 5 average rating, 95 reviews

3 Story Condo - 5 Minutes to Mount Snow!

Quick stats about vacation rentals with outdoor seating in Wilmington

Total rentals
170 properties
Nightly prices starting at
$90 before taxes and fees
Total number of reviews
8.4K reviews
Family-friendly rentals
140 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with a pool
50 properties have a pool

Destinations to explore