Kid-friendly vacation rentals in Windsor County

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Windsor County

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

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Guest favourite

Cottage in Hartland

4.97 out of 5 average rating, 444 reviews

Breeze Hill Cottage

This cozy two bedroom home sits on a rural dirt road overlooking fields, woods, and the NH mountains. Watch birds from the window, relax on the patio, and enjoy the flower gardens. The cottage boasts modern amenities mixed with antiques. Please note: if we don’t respond to an Airbnb message and you need to speak with us, call us on our phones day or night!!! We have had people message us when we were asleep and so we have not been aware and have not responded. Call us! We will hear the phone!

Guest favourite

Guesthouse in Woodstock

4.98 out of 5 average rating, 222 reviews

Cozy Little Spot (Self Check-in)

Contactless check-in. Cozy guest house, cabin-studio-getaway; enjoy the sounds of a stream outside the window (next to the bed). Views of a larger brook below. The"Cabin"is nestled in the trees giving a feeling of floating above the brook below. The interior is decorated w/family heirlooms gathered from around the country. Nothing fancy, just a cozy simple getaway. 3.25 mi from town. Choose from a variety of activities in town or hop on nearby trails. NO PETS ALLOWED. ZERO CONTACT WITH OWNERS.

Guest favourite

Condo in Killington

4.92 out of 5 average rating, 154 reviews

Renovated 1BR, Walk to Lifts, Covered parking

Our comfortable 1-bedroom condo in Building 3 of the Mountain Green Resort provides a bright yet cozy home base for your Killington getaway. Our condo features a new kitchen, dedicated Wi-Fi, and smart TVs. Conveniently located within walking distance to Snowshead, it's perfect for all your mountain activities. Please note, construction teams are replacing the roof of each bldg 7am-7pm daily through the 1st week of November. Scaffolding is up around the outside and the balcony is unavailable.

Guest favourite

Guesthouse in Springfield

4.85 out of 5 average rating, 344 reviews

Connecticut River-Cozy Cottage

This cozy cottage is located on the beautiful Connecticut River, nestled between fertile farmland and Skitchewaug Mountain with views abound. The cottage design utilizes a small footprint while offering functionality and basic comforts, including a small kitchen. Great for all seasons, close to Okemo, Sunapee, Ascutney and other worthy attractions. Hiking and snowshoeing options at your front door. Secrete fishing and swimming holes located on the property. Boat dock available upon request.

Guest favourite

Guest suite in Hartford

4.91 out of 5 average rating, 352 reviews

Sunny Side Airbnb (dog friendly)

Sunny Side Airbnb is located on a secluded 10+ acre property with plenty of outdoor space for dogs to run around and a short hiking trail with views. The Airbnb is located on the farther end of the house with a deck overlooking garden views, a fire pit, and an open field. Convenient location near shops and restaurants. Just over a mile from I-89 off Rt 4 in Quechee, Vt. A short drive to WRJ and W Lebanon, NH, 9.1 miles to Woodstock, VT, 11 miles to Hanover, NH, and 13.4 miles to DHMC.

Guest favourite

Condo in Killington

4.95 out of 5 average rating, 150 reviews

🎿Cozy Fireplace Condo-Mins. to Everything 🚵

<b>Seeking Adventure?</b> This end unit garden level condo is minutes to Killington AND Pico! Easy access to the Appalachian Trail to ATV, mountain bike, hike, and swim. <b>Relaxing?</b> Work remotely with fast Wi-Fi, hang on the porch swing, or unwind in front of the wood fireplace. Hop in the power adjustable king bed, pull the darkening shades, and turn on the sound machine for restful sleep so you can wake up and do it again! A portion of each stay is donated to VT nonprofits.

Guest favourite

Cottage in Windsor

4.97 out of 5 average rating, 356 reviews

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

Guest favourite

Loft in Hartford

4.97 out of 5 average rating, 150 reviews

Gorgeous, clean studio in brand new building.

Enjoy a well-lit, beautiful stay in the heart of White River Junction. Walking distance to restaurants, bars, art galleries, and all this historic town has to offer. Within a 3-min walk: Tuckerbox, Wolf Tree, Big Fatty’s, Trail Break, Northern Stage, Filling Station, and more. 10 min: Dartmouth College 15 min: Dartmouth Hitchcock Medical Center 25 min: Vermont Law School 45 min: Killington Perfect, cozy place for visiting parents, skiers, traveling nurses, professionals, etc.

Guest favourite

Rental unit in Weathersfield

4.99 out of 5 average rating, 168 reviews

The Loft at Weathersfield

Close to Okemo, The Loft at Weathersfield, is just 1/2 hour south of Woodstock / Hanover area and 22 minutes from Okemo Mountain. The Loft, is located in a private agricultural setting with easy access to Vermont's best biking, hiking, fly fishing, skiing, and many equine trails. The loft is 900 square feet with a kitchen/dining room, living room, full bath, one bedroom with a queen bed and one twin bed. There is a spacious deck off the kitchen and a car port underneath.

Guest favourite

Home in Clarendon

4.96 out of 5 average rating, 262 reviews

Custom 2BR Vacation Retreat in Killington Valley!

Welcome to your new Vermont escape! This custom-built 2BR/1BA pet and smoke free home is nestled in the foothills of the green mountains. Our home sits on a 14 acre lot and is close to hiking, skiing, a horse farm, lakes and Rutland (10 mins). You will love the woodwork, luxury white bedding, floor-to-ceiling windows, massive sunny deck, and peace and quiet. There is plenty of space for family memory making, your peaceful mountain retreat awaits!

Guest favourite

Guesthouse in Hartland

4.95 out of 5 average rating, 949 reviews

Yurt In The Woods - Private Refuge

The Yurt In The Woods is 30 ft in diameter which offers 700 spacious sq. ft. It's surrounded by trees and has a yard. 2 night stays required for all Weekends. I require atleast a two night stay for the whole month of October. There is a "one" night stay fee of $40 Allowed 2 dogs with the agreement to my animal policy & $50 fee WiFi 1,000 megabits per second a fiber network Outdoor Gas grill available May - October

Guest favourite

Rental unit in Rutland

4.96 out of 5 average rating, 556 reviews

Your home away from home

Another glorious time of year in Vermont! Our house is close to the mountains (Killington, Pico, Okemo). You'll love our space for its central location to lakes, hiking, restaurants and dining, downtown, art and culture, shopping and medical facilities.This first floor apartment with its home-like atmosphere has a separate entrance. It is good for couples, small families, solo adventurers, and business travelers.