Family-friendly vacation rentals in Wardsboro

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Top-rated family-friendly rentals in Wardsboro

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

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Guest favorite
The custom home features warm wood siding and a welcoming porch with flower boxes. A spacious deck with rustic railings extends from the second floor, while a covered area includes seating. Surrounding greenery enhances the natural setting, creating a serene outdoor ambiance.
Cabin in Wardsboro
4.85 out of 5 average rating, 164 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.

Top guest favorite
A cozy tiny cabin, constructed with wooden beams and a sloped roof, is situated among tall trees. The porch features a railing, inviting seating, and a lantern. Sunlight filters through the foliage, casting a soft glow on the forest floor covered in pine needles.
Treehouse in Brookline
4.98 out of 5 average rating, 257 reviews

Glamping Cabin with Hot Tub on Flower Farm

<b>Vermont's Most Wish Listed</b> ﹏﹏﹏ Nestled in a wooded grove on Tanglebloom Flower Farm, this unforgettable glamping-inspired farm stay invites you to escape the everyday & immerse yourself in nature - comfortably. Designed with a clear roof looking up to the trees and screened sides to let in the breeze, the handmade tiny cabin invites you to slow down. Explore southern Vermont's hikes, farmer's markets & swimming holes or stay put. Perfect for a romantic couples retreat or solo getaway.

Guest favorite
Condo in Dover
4.92 out of 5 average rating, 118 reviews

Base of M.S. All Seasons Fun. Deck/HotT/Pool/Sauna

Sunsil Loft @ MountSnow, your ideal Getaway. Walk to the Base. Unbeatable access to skiing, hiking, biking. Vermont never stops to surprise you with its outdoor adventures, great food and views. The loft offers a cozy gas fireplace, private deck. The kitchen has all you need to prep meals. You also have access to the pool (Summer), sauna, hot tub and GYM. Whether you’re skiing, hiking and biking in summer, or enjoying the fall foliage, our loft is your perfect home base in the Green Mountains.

Top guest favorite
Tiny home in Wilmington
4.99 out of 5 average rating, 346 reviews

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

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, 280 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
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, 1,312 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
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
5 out of 5 average rating, 205 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, water, coffee, tea, milk, fresh eggs + homemade soap. It has an indoor compost toilet, outhouse + outdoor shower (May-Oct) Most seasons, the cabin is 100ft from parking, but weather conditions may require an 800 ft walk from parking at main house.

Top guest favorite
A cozy living area features a mixture of seating options, including a tufted sofa and a vintage-style sofa adorned with decorative cushions. Natural wood floors enhance the warmth of the space, while artwork on the walls and a circular coffee table complete the inviting atmosphere.
Barn in Chester
4.99 out of 5 average rating, 716 reviews

Inviting studio apartment above barn in Vermont

This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. I am as close or as far away as you would like me to be with my house right next door.

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
4.95 out of 5 average rating, 610 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 charming red cabin is positioned amidst lush greenery, with a wraparound deck accessible from the front. Bright yellow flowers bloom in abundance in the foreground, enhancing the natural beauty of the serene setting.
Cabin in Newfane
4.95 out of 5 average rating, 208 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.

Guest favorite
An open living area features rustic wooden beams and warm lighting. A cozy sofa is positioned near a wood stove, with a small dining table adjacent. The kitchen is visible in the background, showcasing appliances against a backdrop of exposed brick and wood floors.
Cottage in Dover
4.85 out of 5 average rating, 326 reviews

Cozy Camp in Vermont

This cozy camp located in beautiful East Dover, is on a secluded road off the beaten path where the babbling brook can be heard. Close to Mount Snow, Lake Whitingham, Lake Raponda, and only 25 minutes to Brattleboro the adventures are endless! Visit the serenity and beauty of Southern Vermont- especially in Fall during “leaf peeping”. This is a camp-style cottage with rustic charm. Snow tires are a MUST- Nov. - Apr.

Top guest favorite
A spacious living area features a large sectional sofa adorned with cozy throw pillows, complemented by a textured area rug. Natural light pours in through expansive windows, enhancing the inviting atmosphere. A side table and a plush armchair add to the comfortable seating options.
Condo in Dover
4.99 out of 5 average rating, 128 reviews

Winter Dream! The Handle Lodge at Snowtree Condos

The Handle Lodge at Snowtree Condos is a modern 1BR condo at the base area of Mount Snow. Comfortably sleeps 6 adults and is fully equipped with everything you'll need for a fun getaway with friends and family. Make a meal in the beautiful kitchen or step out on the balcony for stunning mountain views. Our modern and cozy decor, the lovely views, and proximity to the mountain make it a great place to relax and recharge.

Popular amenities for Wardsboro family-friendly rentals

When is the best time to visit Wardsboro?

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Avg. priceﺩ.ﺇ1,359ﺩ.ﺇ1,458ﺩ.ﺇ1,183ﺩ.ﺇ922ﺩ.ﺇ948ﺩ.ﺇ856ﺩ.ﺇ973ﺩ.ﺇ933ﺩ.ﺇ959ﺩ.ﺇ948ﺩ.ﺇ1,021ﺩ.ﺇ1,326
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Quick stats about vacation rentals that are family-friendly in Wardsboro

  • Total vacation rentals

    Explore 90 vacation rentals in Wardsboro

  • Nightly prices starting at

    Wardsboro vacation rentals start at ﺩ.ﺇ441 per night before taxes and fees

  • Verified guest reviews

    Over 4,770 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Wardsboro vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Wardsboro rentals

  • 4.8 Average rating

    Wardsboro stays are highly rated by guests—averaging 4.8 out of 5!