Kid-friendly vacation rentals in Windham County

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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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Top guest favorite

The cabin's exterior showcases a warm wooden facade with large, strategically placed windows. A spacious screened porch extends from the building, inviting natural light and outdoor enjoyment. A stone pathway leads to the entrance, surrounded by landscaped gravel and native vegetation.

Cabin in Jamaica

5 out of 5 average rating, 242 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.

Guest favorite

A spacious bedroom features a king-sized bed adorned with colorful pillows, framed by large windows that offer views of the surrounding greenery. A decorative bench at the foot of the bed displays neatly arranged towels, complemented by bedside lamps on either side.

Guesthouse in Jamaica

4.95 out of 5 average rating, 155 reviews

The Chick Inn

This is a two-story, renovated barn adjacent to the chicken coop in rural Vermont with views of the forests. It has brand new floors, a new kitchenette, and fresh look. (Some renovation is still taking place.) The chicken coop is just next door but the birds are free-range and range they will. Enjoy a private, hot shower in the garden, just outside. This listing is only suitable for people comfortable with dogs, cats, and chickens which will undoubtedly greet you outside during your stay.

Top guest favorite

The cabin features a wooden exterior surrounded by lush greenery, with large windows allowing natural light to enter. A wooden deck extends from the side, leading to a cozy outdoor area and an adjacent structure, contributing to the rustic charm of the setting.

Tiny home in Dover

4.99 out of 5 average rating, 181 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.

Superhost

The exterior of a wooden cabin is displayed amidst a snowy landscape. The structure features a sloped roof with skylights and a covered entrance that offers protection from the elements. A vehicle is parked nearby, and snow covers the ground and surrounding trees.

Cottage in Putney

4.82 out of 5 average rating, 270 reviews

The Cottage, a house built for guests.

In the village there is a wonderful farm to table restaurant, the Gleanery. A local pub, friendly, great food with indoor and outdoor dining & pub. The General Store, is the oldest continually run general store in Vt. The Next Stage, Yellow Barn, Sandglass Theater, these places provide an amazing collection of visual, musical, spoken word and world renowned art and artist to experience. These cultural event locations are but a mile away for the Cottage I hope you choose for your stay.

Guest favorite

The compact kitchen features modern appliances, including a microwave and refrigerator, paired with wooden cabinetry and a dining area. Light-colored wood flooring extends throughout, and a staircase leads to the sleeping loft above. Decor elements include framed artwork and a vase of flowers positioned on the counter.

Tiny home in Brattleboro

4.87 out of 5 average rating, 156 reviews

Sweet Vermont Tiny Home Get Away

Your unique Vermont retreat is just a click away! Come stay in this custom built tiny house in southern Vermont. We are an easy walk to the train station, art museum, restaurants, shops, and many beautiful nature spots in and around Brattleboro VT, plus a 40 minute drive to the Mount Snow ski area, and local hiking, swimming, boating, skiing, and skating opportunities. A nature lover's paradise! Enjoy the great outdoors and small town living, or cozy up in the tiny house and just relax.

Guest favorite

An inviting interior space features a cozy seating area with a dark couch and a glass coffee table. Natural light enters from a door leading outside, and a wood stove is prominently positioned next to a dining table, enhancing the rustic feel of the camper.

Camper/RV in Guilford

4.93 out of 5 average rating, 134 reviews

Monadnock Sunrise Forest Hideaway

Enjoy a converted camper as your private getaway in Southern VT. Less than 10 min to downtown Brattleboro, yet nestled in the woods for a quiet retreat. Full galley kitchen and living/lounge area. Wood stove for primary heating (electric backup for not so cold days). Outdoor spaces include a fire pit, deck, pool table, hot outdoor shower, outhouse (composting toilet), and forest for galavanting. The place is a perfect fit for up to two adults and one kid (63" long fold down couch).

Guest favorite

The tiny house exterior features a charming porch with colorful railings and vibrant green doors. Tall trees surround the cottage, and a light dusting of snow covers the ground, adding to the serene atmosphere of the setting.

Tiny home in Jamaica

4.94 out of 5 average rating, 1,261 reviews

Apple Blossom Cottage: A Tiny House

The ABC is located just 15 minutes from the Stratton Mountain Gondola and just 2 miles from the popular Jamaica State Park. Comfortable for up to 5 people. The private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, fire pit and porch. The calendar is accurate. Stratton Mountain Resort 10 miles Grace Cottage Hospital 7 miles Magic Mtn 15 miles Bromley 18 miles Mount Snow 15 miles Brattleboro 24 miles Okemo 30 miles Killington 47 miles

Top guest favorite

An elevated wooden deck is surrounded by trees, featuring a canvas tent. Two red folding chairs are positioned nearby, alongside a hammock suspended between two posts. Sunlight streams through the leaves, highlighting the natural setting.

Treehouse in Guilford

4.99 out of 5 average rating, 141 reviews

Cozy tent in the trees on organic flower farm

Tuck yourself into a mature oak forest on the field’s edge of our flower farm, Tapalou Guilds. All-weather canvas tent is pitched with a comfy king mattress inside. Three elevated decks with chairs and a hammock give you options for relaxing and steeping in the forest vibe. Fully equipped outdoor kitchen with propane gas range. We provide potable water from our well. Outdoor shower with on-demand hot water. Simple outhouse with sawdust composting system is clean and convenient.

Top guest favorite

The garden features raised vegetable beds surrounded by a wooden fence. In the background, the charming former church building with a pointed steeple is visible, framed by vibrant autumn foliage in shades of red and orange.

Guest suite in Brattleboro

4.94 out of 5 average rating, 581 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.

Top guest favorite

A modern home is situated on a sloped driveway surrounded by trees, with a green lawn and landscaped stone features. Solar panels are visible on the roof. Two vehicles are parked under a covered deck, which extends from the main structure.

Apartment in Brattleboro

4.95 out of 5 average rating, 173 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.

Guest favorite

A winter scene showcases a blanket of fresh snow covering a serene outdoor area. Snow-laden trees stand in the background, while the foreground features untouched snow with a subtle pathway. The home’s eaves are capped with snow, blending harmoniously with the landscape.

Apartment in Newfane

4.87 out of 5 average rating, 144 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.

Top guest favorite

A cozy studio space features a queen bed with a checkered duvet and a roll-out twin bed nearby. A small dining table is set with two chairs. The kitchenette includes a stove and refrigerator, complemented by a vintage wood-burning fireplace and stone wall.

Guest suite in Newfane

4.93 out of 5 average rating, 207 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. Starlink wifi.