Family-friendly vacation rentals in Windham County

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Top-rated family-friendly rentals in Windham County

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

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Top guest favorite

A spacious bedroom features a skylight that allows natural light to fill the space. A bed is adorned with a colorful floral quilt, while a cozy armchair and table create a relaxing sitting area by glass doors that offer a view of the surrounding greenery.

Cottage in Newfane

4.97 out of 5 average rating, 135 reviews

Silk Purse Cottage on Baker Brook

The "Silk Purse" started life in the 60's as a 10x40 mobile home. Its placement next to Baker Brook offers a private view out of every window and easy vehicle access. The screened porch is a relaxing place to have coffee or cocktails. Extra windows add interior light in this shaded woodland setting, and a beautiful 12x14 addition with a skylight and a full wall of glass give an unobstructed, private view of the stream. 20 minutes to Brattleboro, 30 to Stratton, 25 to Mt. Snow, 40 to Magic Mt!

Guest favorite

A cozy outdoor living area features wooden seating, including a swing and chairs surrounding a fire pit. The camper is positioned on a deck nestled among trees, providing a sense of seclusion. A small table is visible, completing the inviting gathering space.

Camper/RV in Guilford

4.94 out of 5 average rating, 160 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 two adults (queen bed) and one kid (63" long fold down couch).

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

4.99 out of 5 average rating, 256 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.

Top 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, 167 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, 190 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, 277 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.

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, 161 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

A spacious great room features a comfortable seating area with a white couch, eclectic armchair, and colorful floor design. Artistic decorations are placed on the walls and shelves, with a kitchenette visible in the background. A piano and drums are positioned nearby for guest use.

Guest suite in Wilmington

4.92 out of 5 average rating, 787 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!

Guest favorite

A living area features warm wooden walls and large windows draped with sheer curtains, allowing natural light to fill the space. A comfortable sofa sits adjacent to a television, with a vintage chest and decorative items adding character. A patterned area rug enhances the cozy ambiance.

Apartment in Newfane

4.87 out of 5 average rating, 154 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, 214 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.

Guest favorite

A loft sleeping area features a queen size bed with a patterned quilt. Three large windows allow natural light to illuminate the space, offering views of the treetops outside. The wooden railing adds a rustic touch to the cozy setting.

Guest suite in Newfane

4.9 out of 5 average rating, 363 reviews

Cozy Apartment

We love our home on a dead end dirt road, quiet and private, yet close to all you need and want when you think of VT. Ski (Mt. Snow or Stratton), hike, swim, enjoy local fare at great restaurants or shop the Brattleboro Farmer's Market or food coop. Enjoy a swim at the covered bridge in Dummerston or at the convergence of the Rock and the West Rivers. Or drive up Newfane Hill to Kinney Pond.

Guest favorite

A spacious living area features a large, brown leather sofa positioned around a central area rug. Plants are placed throughout, with a decorative mirror and artwork on the walls. A television is situated on a low table, enhancing the cozy atmosphere.

Apartment in Town of Rockingham

4.96 out of 5 average rating, 215 reviews

Gorgeous 1-Bedroom Space in Historic Bellows Falls

Enjoy a stylish experience at this centrally-located place. Bellows Falls is a historic village located in Southern Vermont. Once a booming mill town, now a quaint picturesque village with shops, restaurants, and more. The space is located right in the center of town with plenty of space for those seeking to unwind in a small New England village.