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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

4.87 out of 5 average rating, 104 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.

Guesthouse in Brattleboro

4.98 out of 5 average rating, 219 reviews

Light Filled Loft in the Vermont Countryside

Our spacious, tranquil, light-filled Barn Loft is thoughtfully and creatively designed. Complete with a living area, sleeping alcove, flat-screen TV, full kitchen, dining area, and large bathroom with a deluxe shower. A private deck with seating that looks out into our lovely Vermont woods and verdant gardens is attached to the loft. Stay a night or a week, there is plenty to do in every season. We are a friendly, welcoming, worldly, family. We look forward to hosting you at our country home.

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, 153 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.

Tiny home in Dover

4.99 out of 5 average rating, 168 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, 285 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, 294 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, 207 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 Dummerston

4.91 out of 5 average rating, 435 reviews

Rice Farm Retreat

Peaceful, romantic retreat in this stunningly large, 1850's remodeled barn apartment. The historic barn 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.

Guest suite in Newfane

4.93 out of 5 average rating, 204 reviews

Cute studio apt on historic VT farm

Spend some time on a historic farm in Southern Vermont. Visit with pigs and chickens, walk around on country roads, take a dip in swimming holes, wildlife abounds! Super-relaxing setting in beautiful Mother Nature and well-equipped accommodations with everything you need. The self-contained little studio has a separate entrance. Full kitchen and bath, queen bed plus a roll-out twin. Excellent heater. Wifi is enough for basic tasks, but not for 8 hours of daily zoom.

Guest suite in Brattleboro

4.94 out of 5 average rating, 555 reviews

Charming studio in renovated 19th century church.

This spacious studio apartment is located in the former Swedish Congregational Church in historic Swedeville, a secluded hilly neighborhood built by Swedish immigrants in the 1800's. For years it housed Rick and Liza’s stained glass studio, which they have now lovingly and creatively transformed into a residence. The rental is minutes from the interstate and one mile from downtown Brattleboro, but the neighborhood has a rural and somewhat European flavor to it.

Guesthouse in Putney

4.97 out of 5 average rating, 270 reviews

Cozy cottage loft and retreat

Relax and recharge in our peaceful Vermont cottage. Enjoy this sweet getaway with hardwood floors, fast wifi, a fully equipped kitchen, a quiet sleeping loft with a queen size bed, gorgeous natural light, views of surrounding hills and pond, gardens, and your own private entrance and back deck next to the Putney Brook.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Chalets

Adventure-ready homes with après-ski style

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, 170 reviews

Frosted Willows

Home in Wardsboro

4.95 out of 5 average rating, 100 reviews

Hot Tub & Game Room - Ski Mt. Snow/Stratton

Home in Wilmington

4.99 out of 5 average rating, 189 reviews

Vermont Sugar House Retreat

Home in Readsboro

4.86 out of 5 average rating, 124 reviews

December in Peaceful Vermont (Pet Friendly)

Home in West Brattleboro

4.93 out of 5 average rating, 108 reviews

Modern Spacious Home with Mountain Views

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

Kid-friendly apartment rentals

Rental unit in Vernon

4.96 out of 5 average rating, 153 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, 172 reviews

Apartment on Main Street

Rental unit in Guilford

4.88 out of 5 average rating, 395 reviews

Apartment with a view

Rental unit in Town of Rockingham

4.95 out of 5 average rating, 254 reviews

Stunning Studio in historic Downtown Bellows Falls

Rental unit in Brattleboro

4.96 out of 5 average rating, 305 reviews

Apt in town 2 BR/2 levels in Victorian Farmhouse

Rental unit in Brattleboro

4.89 out of 5 average rating, 538 reviews

Cozy, Private & Great location for exploring VT !

Rental unit in Jamaica

4.85 out of 5 average rating, 201 reviews

The Getaway

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 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, 149 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

4.78 out of 5 average rating, 94 reviews

Cozy Mount Snow 1 Bed : Hot tub, Sauna, Deck

Condo in Dover

4.84 out of 5 average rating, 157 reviews

Mount Snow Close, Great Price, Lots of Room

Destinations to explore