Kid-friendly vacation rentals in Shaftsbury

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Top-rated kid-friendly rentals in Shaftsbury

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Guest favorite

Apartment in Bennington

4.94 out of 5 average rating, 154 reviews

NEW Escape the City- Vermont Studio

Our newly renovated studio apartment is located minutes from Bennington College, and sits on 7 acres of land in the Green Mountain National Forest. It's on the second floor of our home through a private entrance with a personal deck and outdoor seating. Take an afternoon to stroll to the Mile Around Woods, or hike to the white rocks! Walk the Ninja trail from the college to see the historic covered bridges, or drive 20-30 miles N to enjoy Vermont's best skiing, and shopping at designer outlets!

Jan 8 – 15

ﺩ.ﺇ346 per night

Guest favorite

Cabin in Shaftsbury

5.0 out of 5 average rating, 373 reviews

The Vermont Dream Cabin on 70 Acres

*4 WHEEL/AWD a MUST for WINTER BOOKINGS* Authentic log cabin on 70 acres+ of pristine Vermont forest with hiking/snowshoe trails, river & mountain stream. Cozy up with wine, games or a book by the huge stone woodburning fireplace with fav music from the vintage Bose stereo, enjoy coffee & stargazing on the rocking porch while taking in the mountain views & wildlife or explore the forest & river trails. Enjoy making meals in the ample fully stocked kitchen, the outdoor grill & around the campfire

Mar 25 – Apr 1

ﺩ.ﺇ904 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.ﺇ722 per night

Guest favorite

Home in Bennington

4.99 out of 5 average rating, 278 reviews

Southern Vermont Home

Beautiful home that offers privacy on over one acre of land. It is only a short drive to the conveniences of downtown shopping, restaurants, Bennington College, and much more. This house is 35 minutes from Manchester's famous outlets, 20 minutes from Williamstown, MA, and 45 minutes from Albany, NY. Bromley and Mount Snow ski areas are 40 minutes. The home has wonderful finishes and you will feel right at home upon arrival. Please come explore Vermont from our country escape!

Nov 1 – 8

ﺩ.ﺇ795 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.ﺇ578 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.ﺇ460 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.ﺇ1,627 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.ﺇ609 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.ﺇ428 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.ﺇ836 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.ﺇ1,404 per night

Guest favorite

Apartment in Bennington

4.91 out of 5 average rating, 163 reviews

Scenic Vermont Studio

This beautiful retreat is halfway between the ski slopes of southern Vermont and the cultural centers of Williamstown and North Adams, MA. The residence is a modern, spacious, basement apartment, part of an 1860 farm house. It has its own private entrance around the back of the house at ground level. Solar garden lights and motion detector lighting will illuminate your path to the apartment.

Jun 12 – 19

ﺩ.ﺇ378 per night