Vacation rentals with outdoor seating in Shaftsbury

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Top-rated outdoor seating rentals in Shaftsbury

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Guest favorite

Cabin in Shaftsbury

4.99 out of 5 average rating, 205 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!

Aug 31 – Sep 7

ﺩ.ﺇ1,144 per night

Guest favorite

Home in Shaftsbury

4.84 out of 5 average rating, 106 reviews

Quaint One-Story Vermont House with Mountain View

From our quaint one-story house, you can see a variety of scenery, from the bright changing colors of the leaves in the autumn to the soft piles of snow in the winter. Experience the quiet of the nearby woods, and see roaming animals such as deer or turkey. Make sure to stop at one of the nearby lakes, each of which offers a variety of amenities, and lush scenery. In the winter, keep warm in the cozy living room next to the fireplace, while having a chat with your friends and family.

Jan 28 – Feb 4

ﺩ.ﺇ707 per night

Guest favorite

Guesthouse in North Bennington

4.98 out of 5 average rating, 152 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, air conditioned 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. Please note that due to a severe allergy, we cannot accommodate animals.

Jul 19 – 26

ﺩ.ﺇ566 per night

Guest favorite

Guest suite in Shaftsbury

4.99 out of 5 average rating, 134 reviews

Country Getaway with a Spa/Birds of a Feather Farm

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.

Nov 5 – 12

ﺩ.ﺇ451 per night

Guest favorite

Cottage in Shaftsbury

4.99 out of 5 average rating, 601 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.

Mar 20 – 27

ﺩ.ﺇ1,594 per night

Guest favorite

Cabin in Shaftsbury

4.9 out of 5 average rating, 382 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!

Dec 2 – 9

ﺩ.ﺇ597 per night

Guest favorite

Apartment in Bennington

4.96 out of 5 average rating, 140 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.

Aug 26 – Sep 2

ﺩ.ﺇ419 per night

Guest favorite

Farm stay in Shaftsbury

5.0 out of 5 average rating, 111 reviews

Wing & A Prayer Farm

Each season at Wing & A Prayer Farm will restore & reset your pace. Situated on a working fiber farm, there are a variety of sheep, goats, alpacas, miniature donkeys, an American Guinea hog named "Princess Peppermint", and poultry-aplenty that decorate the landscape. The privacy of your own shady-glade & glimpses into farm life make this getaway just right. Comfortable, authentic farm coziness with traditional conveniences supports travelers from all walks.

Dec 24 – 31

ﺩ.ﺇ819 per night

Guest favorite

Home in Bennington

4.99 out of 5 average rating, 110 reviews

The Gate House--Experience Vermont!

The Gate House is a historic property located at the foothills of Mt Anthony. Built in 1865, the original structure of the house served as the gate house to the Colgate Estate, one of the most beautiful properties in Southwestern Vermont. Our home is just a few short miles to downtown where you can find local restaurants and breweries. We are not far from some of the best skiing/riding in the Northeast at Mt Snow, Bromley, Stratton and Prospect Mountains.

Jun 10 – 17

ﺩ.ﺇ1,375 per night

Guest favorite

Guesthouse in Cambridge

4.95 out of 5 average rating, 167 reviews

Quiet and Cozy Country Cottage

Very clean, well kept, 1 bedroom country cottage. Hardwood floors in bedroom and kitchen. Propane heater for winter months and AC in the summer. This a very quiet place, great for a relaxing getaway. There is a fire pit on the property, right near the cottage, for evening fires. We recommend AWD or 4WD or vehicles with snow tires during winter months. The cottage is located on a hill, can be slippery in the winter.

Nov 29 – Dec 6

ﺩ.ﺇ421 per night

Guest favorite

Home in Bennington

4.99 out of 5 average rating, 239 reviews

Cozy Modern Sugar House with spectacular views.

This beautiful Vermont home sits on 25 acres with spectacular views. We moved this sugar house structure to this land and had an architect adapt it to its surroundings. It has three walls of windows that display the amazing views. The house is surrounded by Mount Anthony hiking trails and a gorgeous pond. The location is a 5 minute drive to town or a lovely 20 minute walk.

Feb 17 – 24

ﺩ.ﺇ1,093 per night

Guest favorite

Apartment in Bennington

4.93 out of 5 average rating, 529 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.

Sep 2 – 9

ﺩ.ﺇ371 per night