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Kid-friendly vacation rentals in Windham County

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Windham 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.

Rental unit in Putney

4.89 out of 5 average rating, 131 reviews

Hip & Cozy Storefront

Ground-level historic storefront turned into a private, hip place to sleep. Nestled in the village of Putney, VT it is just a walk to restaurants, General Store, nature trails and Next Stage Theater-short drive to Putney School, Landmark College & The Greenwood School- huge bathtub, movie screen, kitchenette with fridge, handicap accessible. Can sleep 3 or more upon request. The ski resorts of Okemo, Mt. Snow, Magic Mountain, and Stratton are not far~ making Putney a perfect ski get-a-way spot.

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.

Cabin in Newfane

4.95 out of 5 average rating, 151 reviews

Cozy Cabin in Southern VT

Take it easy at this tranquil getaway. Fall asleep to chirping bugs and wake up to birdcalls. This is a quiet, lovely cabin in Newfane VT. Read a book, walk the meditation circle, swing in the hammock, and explore all that Southern VT has to offer. Close to swimming holes, hikes, country stores, flea and farmers' markets, and ski mountains (Mt Snow and Stratton) Pets and children are welcome, but there is only one queen bed. We can usually provide a travel crib if requested in advance.

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.

Tiny home in Dover

4.99 out of 5 average rating, 167 reviews

Rustic Cabin in foothills of Green Mountains

Rennsli Cabin is off grid + nestled on a forested plateau in the foothills of the Green Mountains. You will feel like you are in the middle of nowhere, unplugged and able to regenerate. Kitchen is equipped with cooking essentials+ hosts provide water, coffee, tea, milk, fresh eggs + homemade soap. There is an indoor compostable toilet + outhouse + outdoor shower. Most seasons, the cabin is 100ft from parking, but weather conditions may require an 800 ft walk from parking at main house.

Cottage in Dover

4.84 out of 5 average rating, 284 reviews

Cozy Camp in Vermont

This cozy camp located in beautiful East Dover, is on a secluded road off the beaten path. Close to Mount Snow, Lake Whitingham, Lake Raponda, and only 25 minutes to Brattleboro the adventures are endless! Get out of the city and visit the serenity and beauty of Southern Vermont- especially in Fall during “leaf peeping”. This is a camp-style cottage with rustic charm. Newly replaced flooring and a fresh coat of paint in both bedrooms upstairs. Snow tires are a MUST- Nov.-April

Barn in Marlboro

4.95 out of 5 average rating, 293 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.

Cottage in Newfane

4.99 out of 5 average rating, 206 reviews

Cozy Vermont Antique Sugar House with Fireplace

Enjoy a peaceful and unique stay at this beautiful 1796 Sugar House. Luxury bedding, cozy fireplace, soaring timbers to a cathedral ceiling make this a special place. There is a Queen size bed on the main floor and twin beds in the sleeping loft accessible by a ladder. Try some of our wonderful local restaurants and shops. Lots of hiking trails to explore. Winter sports all around, or just enjoy some hot chocolate, a fire, and a good book. You are sure to enjoy the “Sugar House”.

Rental unit in Brattleboro

4.95 out of 5 average rating, 165 reviews

Contemporary forest eco-retreat, mountain views

This is an open, light-filled one-Bdm apartment on the lower level of our hillside home, surrounded by forests, with stunning views. Your space is 719 sf + access to laundry. We are fully vaccinated, and ask the same of guests. If you think you may have Covid please tell us. We welcome all kinds of people, regardless of race, ethnicity, gender, etc. We may ask questions before accepting people who don’t have many prior reviews. We don't take pets, sorry.

Rental unit in Newfane

4.86 out of 5 average rating, 138 reviews

Apartment at Five Ferns

A cozy spot perfect for quick romantic getaways and an equally comfortable base for longer adventures. Views out your windows show perennial flower gardens and trees. Queen mattress in a spacious bedroom, en-suite bathroom (shower), and a living/dining area with an equipped kitchen are all at your service. Enjoy our yard and trails along the river. We are an easy 5 minute drive to a fantastic restaurant and many more within 15 minutes of driving.

Barn in Newfane

4.97 out of 5 average rating, 145 reviews

Beautiful rustic woods and fields retreat.

Within the Fritz Conference Center, tucked into the beauty of the Vermont Countryside, is this charming apartment. Part of a renovated 19th century barn it is the perfect getaway. It sits on over 33 acres of fields, woods, apple orchard and Mountain View’s. 2 miles from historic Newfane Vermont, you are able to enjoy privacy, while close to the many attractions of the area. We are also dog friendly. There is an extra fee of $80 per trip per dog

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 Windham County kid-friendly rentals

Free parking on premises

Air conditioning

Kid-friendly house rentals

Home in Dummerston

4.99 out of 5 average rating, 338 reviews

Pinecone Pond

Home in Brattleboro

4.95 out of 5 average rating, 166 reviews

Frosted Willows

Home in Putney

4.99 out of 5 average rating, 208 reviews

Lovely Brick Schoolhouse

Home in Wilmington

4.99 out of 5 average rating, 187 reviews

Vermont Sugar House Retreat

Home in Wilmington

4.94 out of 5 average rating, 259 reviews

Wilmington. Easy walk to center of town.

Home in Newfane

4.98 out of 5 average rating, 130 reviews

Peaceful cabin close to skiing & Brattleboro

Home in Chesterfield

4.9 out of 5 average rating, 103 reviews

Governer's Brook Camp - 2 Bedroom

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 Londonderry

4.92 out of 5 average rating, 349 reviews

Cozy Suite in a Historic Building Near Ski Resorts

Rental unit in Town of Rockingham

4.97 out of 5 average rating, 180 reviews

Gorgeous 1-Bedroom Space in Historic Bellows Falls

Rental unit in Brattleboro

4.9 out of 5 average rating, 350 reviews

Quiet St in Town, gardens, terrace

Rental unit in Vernon

4.96 out of 5 average rating, 152 reviews

Farm land view.

Rental unit in Wilmington

4.92 out of 5 average rating, 115 reviews

Walk To Wilmington Village

Rental unit in Town of Rockingham

4.82 out of 5 average rating, 171 reviews

Apartment on Main Street

Rental unit in Guilford

4.88 out of 5 average rating, 393 reviews

Apartment with a view

Rental unit in Putney

5 out of 5 average rating, 102 reviews

Peaceful Forest Studio

Kid-friendly condo rentals

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 Stratton

4.96 out of 5 average rating, 129 reviews

Cozy condo within walking distance to the slopes.

Condo in Dover

4.87 out of 5 average rating, 99 reviews

⛷ Walk to Mt. Snow-Spa-Pool-Fireplace ⛷

Condo in Dover

4.84 out of 5 average rating, 157 reviews

Mount Snow Close, Great Price, Lots of Room

Destinations to explore