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Kid-friendly vacation rentals in Bennington County

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Bennington County

Guests agree: these kid-friendly rentals are highly rated for location, cleanliness, and more.

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Cabin in Wardsboro

4.86 out of 5 average rating, 100 reviews

Mountain side acres

10 years of love and affection went into building our 2 bedroom custom home. Sticking with natural products to blend together the beauty of the surrounding area. Lay in bed at night and listen to river that runs the entire length of the property. The house has a full kitchen with seating for 6. Spacious living room for relaxing or admiring one of the many birds that visit all year round. Two upstairs bedrooms and office space. Walkout basement with full entertainment area, hot tub,exercise room.

Cabin in Woodford

4.91 out of 5 average rating, 141 reviews

Lakeview Cabin in the Mountains - beautiful

Lovely log sided cabin situated across from Woodford lake with view. Large Great room cathedral ceiling, halfmoon window, pine ceiling & floors, dining table,woodstove, corner gas fireplace, full kitchen. Beautiful ambiance, rustic yet elegant. 2 bedrooms, full bath with clawfoot tub, romantic sleeping loft w sitting area. Basement play area heated with 2 beds for children. Central heat, washer/dryer TV/Roku, ceiling fans. Great getaway for nature lovers, skiers, snowmobilers, hikers. Wifi.

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 Manchester

5 out of 5 average rating, 212 reviews

Private two-bedroom suite within a two-story house

This is a private suite located on the second floor of a house. Separate entrance. The owners live downstairs. Great location with mountain views. Please note: 1) Our kitchen is fully equipped, but it has a hot plate instead of the traditional stove. 2) Instead of a full-size living room there is a small sitting area with a TV in the same area where the kitchen is located. 3) Guests don't have access to the backyard/patio, but you can enjoy the outside seating set in front of the house.

Guesthouse in North Bennington

4.99 out of 5 average rating, 210 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, 144 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 .

Guesthouse in Arlington

4.98 out of 5 average rating, 153 reviews

Cozy Log Cabin Suite [100+ Reviews 4.98 Rating]

Welcome to a cozy log cabin loft on private property. Our 600+ square foot suite is consistently upgraded for our guest. You'll enjoy high end accommodations, solid wood flooring, AC, 50" TV with Cable, wireless internet, premium King size bed, fridge and kitchen. Cleanliness has always been a top priority for our guests. We are proud to hold a 5-star rating. As a Registered Nurse in our local hospital, I can assure you we are cleaning and disinfecting following the CDC guidelines.

Cottage in Shaftsbury

4.98 out of 5 average rating, 639 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, 154 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.

Rental unit in Bennington

4.95 out of 5 average rating, 152 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, 750 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 Arlington

4.87 out of 5 average rating, 134 reviews

Brian Peace of Heaven

Beautiful Mountain View 4 1/2 Acres Park your vehicle inside garage upstairs studio apt with full kitchen and Bathroom with shower. There 100 acres to the right and 40 to the left. welcome to Brian’s peace of Heaven.. There skiing 10miles a way Stratton and Bromley. Out let’s Stores in Manchester Vt . Roads are always plowed in winter. Pellet stove that you can use with Gas heat and hot water. 2 beds queen size and Full size.

Vacation rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Bennington County kid-friendly rentals

Free parking on premises

Air conditioning

Kid-friendly house rentals

Home in Shaftsbury

4.85 out of 5 average rating, 118 reviews

Quaint One-Story Vermont House with Mountain View

Home in Londonderry

4.98 out of 5 average rating, 114 reviews

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

Home in Wilmington

4.99 out of 5 average rating, 187 reviews

Vermont Sugar House Retreat

Home in Bennington

4.99 out of 5 average rating, 124 reviews

The Gate House--Experience Vermont!

Home in Readsboro

4.86 out of 5 average rating, 124 reviews

Relax in Peaceful Vermont! (Pet Friendly)

Home in Wilmington

4.94 out of 5 average rating, 259 reviews

Wilmington. Easy walk to center of town.

Home in Pownal

4.97 out of 5 average rating, 235 reviews

Cozy Vermont mini-house

Home in Jamaica

4.86 out of 5 average rating, 277 reviews

Yellow Sweetie at the Base of Stratton

Kid-friendly apartment rentals

Rental unit in Pownal

4.94 out of 5 average rating, 114 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 Manchester

4.94 out of 5 average rating, 110 reviews

Arrowhead Stays - Downtown Manchester Vermont

Rental unit in Wilmington

4.93 out of 5 average rating, 181 reviews

Quaint cozy vermont apartment

Rental unit in Manchester

4.92 out of 5 average rating, 24 reviews

Manchester Cottage

Rental unit in Manchester

4.99 out of 5 average rating, 212 reviews

Style and Comfort- Perfect Year Round Location

Rental unit in Dorset

4.99 out of 5 average rating, 185 reviews

Vermont barn apartment

Kid-friendly condo rentals

Condo in Manchester

4.96 out of 5 average rating, 25 reviews

Above the Mat - Downtown 1 Bedroom Condo

Condo in West Dover

4.75 out of 5 average rating, 132 reviews

Beautiful condo 2.5 miles from Mount Snow

Condo in Dover

4.87 out of 5 average rating, 228 reviews

Mt Snow Ski In/Out at Seasons

Condo in Dover

4.99 out of 5 average rating, 105 reviews

Winter Dream! The Handle Lodge at Snowtree Condos

Condo in Dover

4.87 out of 5 average rating, 76 reviews

Cute, Cozy Condo at the base of Mount Snow

Condo in Stratton

4.94 out of 5 average rating, 148 reviews

Updated Ski in/Ski out Stratton Condo!

Condo in Dover

4.94 out of 5 average rating, 36 reviews

Ski in Ski out condo great location

Condo in Stratton

4.96 out of 5 average rating, 129 reviews

Cozy condo within walking distance to the slopes.

Destinations to explore