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Vacation rentals with outdoor seating in Bennington County

Find and book unique outdoor seating rentals on Airbnb

Top-rated outdoor seating rentals in Bennington County

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

Relax 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! ☺

Tiny home in Wilmington

4.99 out of 5 average rating, 203 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, 215 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.

Chalet in Dover

4.92 out of 5 average rating, 285 reviews

A charming VT chalet

Charming chalet nestled in the Mt Snow valley. Relax to the sound of a babbling brook in the back yard while you hang around a stone fire pit! Unwind in the quiet serenity of this country home complete with fully equipped kitchen with a newly installed gas fireplace , a comfy open living room with flat screen cable tv & DVD player Roko & High speed Internet . We have a lock box located on the post near the front entrance. combo provided upon arrival . Washer & dryer located on first level.

Cabin in Shaftsbury

4.99 out of 5 average rating, 237 reviews

The Hygge Loft- mid-mod cabin on 70 forested acres

The Hygge Loft: a midcentury modern-designed cabin nestled among 70 acres of privately-owned forest with rivers & hiking trails. Enjoy sipping an espresso or wine while listening to vinyl records, cozied up by the wood-burning fireplace. Take a walk in the forest to the river or stargaze by the firepit on the private deck. Indulge in a luxurious bath or snuggle up in the ultra comfy king-size bed with views of treetops and sky all around. It’s the kind of place you’ll never want to leave!

Guesthouse in North Bennington

4.99 out of 5 average rating, 205 reviews

Birch House - lake, green trees + modern comforts

We're a little guest house near a lake in Vermont with green trees + modern comforts. Perfect for couples + individuals looking to relax + enjoy nature. Renovated, light space with cozy, minimalist vibes. A small modern cabin that's peaceful + private. Tucked into a quiet neighborhood. Main home is a separate building next door. Near Bennington College. 12 minutes to downtown Bennington. IG birchhousevt Please note that due to a severe allergy, it is difficult to accommodate animals.

Farm stay in Bennington

4.97 out of 5 average rating, 141 reviews

The Farm cottage

Take a break and unwind at this little peaceful oasis. A little bit of the country is right beside you with the neighing of horses and the clucking of chickens who roam our property. We are close to Bennington College and great restaurants and Robert Frost house. We are 35 minutes from Manchester that has some great restaurants and shopping. Bromley ski resort is just beyond Manchester in Peru Vermont . It is a year around resort with water slides in summer and skiing in winter .

Cottage in Shaftsbury

4.98 out of 5 average rating, 636 reviews

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

This newly-renovated historic schoolhouse overlooks our family's regenerative organic farm. The Schoolhouse is bright & open, with a modern design & peaceful, rustic feel. It is the perfect place to relax & enjoy a country setting with views of the Green Mountains in every direction. We have added a new private deck at the Schoolhouse property, with a hot tub & panoramic barrel sauna. Come to unwind, cook, & enjoy a quintessential Vermont experience on our 350 acre property.

Guest suite in Shaftsbury

4.99 out of 5 average rating, 153 reviews

Peaceful Stay at Birds of a Feather Farm & Spa

Our cozy upstairs studio can accommodates up to 4 and is separate from the main house. Plush towels, linen, pillows and blankets. Kitchenette is fully stocked with everything you need for cooking. The private entrance is equipped with punch key lock to facilitate easy self check-in. A queen size sleep number bed, queen size pullout couch, table with four chairs, a dresser, one bathroom with shower, smart TV and WIFI. Heat and cooling. A spa is available and infrared sauna.

Cabin in Shaftsbury

4.9 out of 5 average rating, 399 reviews

The LoveNest -Charming private cabin on 65 acres

The Love Nest has returned! We’re high up on the hill yet close to art and culture, great views, restaurants and dining, family-friendly activities, skiing, Bennington, Manchester VT close by. Williamstown Mass not far. A huge yard. You’ll love my place because of the coziness, the light, the comfy bed, the well equipped kitchen, privacy and views, the extreme quiet and relaxation. Waterfalls! My place is good for couples, solo adventurers, and dog guests. 420 friendly!

Rental unit in Bennington

4.95 out of 5 average rating, 151 reviews

Cooper's Place

Small bright and cozy apartment nestled in the Shires of Vermont. A mid-modern space with VT flare and all of the amenities you need to enjoy your getaway. Housed behind a unique building that was once a manufacturer of concrete blocks and is still a hardscape retail store located in downtown Bennington called Morse Brick & Block. Enjoy the porch or have a fire in the fire pit. Take a trip to the Bennington Monument and Museum. Close to hiking trails and ski areas.

Guest suite in Wilmington

4.92 out of 5 average rating, 748 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!

Vacation rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Bennington County outdoor seating rentals

Free parking on premises

Air conditioning

House rentals with outdoor seating

Home in Manchester

4.97 out of 5 average rating, 105 reviews

Modern meets Country Cottage in Manchester Village

Home in Wilmington

4.88 out of 5 average rating, 163 reviews

Adams Farm-"The Little Farmhouse"

Home in Londonderry

4.98 out of 5 average rating, 112 reviews

Modern 3-bedroom A-frame in Londonderry w/ Pond

Home in Bennington

4.85 out of 5 average rating, 157 reviews

Bennington Guest Barn 3 Bedrooms

Home in Manchester

4.95 out of 5 average rating, 104 reviews

1850 Marble Path House

Home in Wilmington

4.99 out of 5 average rating, 185 reviews

Vermont Sugar House Retreat

Home in Winhall

4.95 out of 5 average rating, 122 reviews

Summit View Ski and Golf Retreat w/hot tub & Sauna

Home in Wardsboro

4.94 out of 5 average rating, 148 reviews

Sawmill Road - between Stratton and Mount Snow

Apartment rentals with outdoor seating

Rental unit in Pownal

4.94 out of 5 average rating, 113 reviews

"The Parlors"

Rental unit in Winhall

5 out of 5 average rating, 12 reviews

Private & Quiet Apartment near Stratton Access Rd

Rental unit in Wilmington

4.98 out of 5 average rating, 463 reviews

**Happy Hour! Gorgeous & Modern Downtown Retreat**

Rental unit in Wilmington

4.93 out of 5 average rating, 180 reviews

Quaint cozy vermont apartment

Rental unit in Manchester

4.91 out of 5 average rating, 23 reviews

Manchester Cottage

Rental unit in Dover

4.81 out of 5 average rating, 80 reviews

*Betimor North Apt.4 Newly renovated Mt. Snow

Rental unit in Dorset

4.83 out of 5 average rating, 121 reviews

Peace Street Guest Apartment

Rental unit in Manchester

4.99 out of 5 average rating, 211 reviews

Style and Comfort- Perfect Year Round Location

Condo rentals with outdoor seating

Condo in Peru

4.96 out of 5 average rating, 82 reviews

Cozy Mountain Condo - True Ski in Ski out

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, 104 reviews

Winter Dream! The Handle Lodge at Snowtree Condos

Condo in Stratton

4.96 out of 5 average rating, 24 reviews

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

Condo in Stratton

4.93 out of 5 average rating, 84 reviews

Great 2 bedroom condo at Stratton Mountain

Condo in Dover

4.94 out of 5 average rating, 35 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

Destinations to explore