Family-friendly vacation rentals in Rutland

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Rutland

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

0 of 0 items showing

1 of 3 pages

Guest favorite

A charming cottage is set against a backdrop of lush trees, with a deck extending from the front. The warm, orange sky creates a serene atmosphere, casting soft light on the exterior of the house and surrounding landscape.

Guesthouse in Hartland

4.96 out of 5 average rating, 189 reviews

Cottage for Two/Solo Getaway/Musician's Retreat

Luxurious, well appointed cottage with beautiful sunrise view located between Woodstock VT and Hanover NH. An inspiring treat for musician’s getaway is a fully restored 1929 Steinway L. Full kitchen, custom cabinets, gas fireplace, energy efficient heat pump, washer, dryer and very comfortable queen bed. A romantic getaway in the woods, a place to relax, work in peace, or explore the beauty and history of the area. Hiking, biking, fly fishing, hot air balloon rides and shopping are all close by.

Superhost

A bright kitchen area is complemented by a vibrant yellow wall. Wooden cabinetry holds kitchen essentials above a small countertop. Two bar stools are positioned at a wooden table. Natural light enters through large windows, illuminating the cozy studio space with an inviting atmosphere.

Apartment in Hartland

4.84 out of 5 average rating, 101 reviews

Private Riverside Studio* Upper Valley*Vermont

This unique place has a style all its own. Perfect for a traveling nurse or anyone who needs a relaxing getaway or a remote place to work. This studio apartment has river and garden views and is conveniently located in the New England Village of North Hartland. A 15-20 minute drive to Dartmouth College or DHMC. Take country walks across the twin covered bridges right from your doorstep. Relax on the front porch and watch the bald eagles and peregrine falcons search for prey along the river.

Guest favorite

The spacious interior of the yurt features a circular design with natural wood and fabric elements. Comfortable seating areas include a queen-sized futon and a wooden sofa. Large windows allow natural light to fill the space, while a wood stove provides warmth.

Guesthouse in Hartland

4.95 out of 5 average rating, 1,008 reviews

Yurt In The Woods - Private Refuge

The Yurt In The Woods is 30 ft in diameter - 700 spacious sq. ft. It's surrounded by trees and has a yard. 2 night stays required for all Weekends. I require at least a two night stay for the whole month of October with the exception of October 3rd. There is a "one" night stay fee of $50 Allowed 2 dogs with the agreement to my animal policy & $50 fee WiFi 1,000 megabits per second a fiber network Outdoor Gas Grill , Outdoor Fire Circle, and Outdoor Shower available May - October

Guest favorite

A recently renovated property is set against a backdrop of lush greenery, featuring a well-maintained lawn and blooming flower beds. The exterior showcases a gray siding, with several large windows allowing natural light into the inviting interior.

Guest suite in Brownsville

4.89 out of 5 average rating, 134 reviews

Newly renovated private space on Ascutney Trails

Newly renovated private space on Ascutney trails--walking distance Ascutney Outdoors Center, hotel, Maple Kitchen Restaurant, skiing, and Brownsville Butcher & Pantry. Trail access in back yard with miles of hiking, mountain biking, running and skiing. Parking for 2 cars. Close to Woodstock shops and Okemo adventure center. Private keycode entrance with self-check in. Microwave, refrigerator, Keurig, coffee and tea provided. Air conditioned during the summer. Television and fast wifi.

Guest favorite

A modern cabin is situated among trees, surrounded by greenery. Two Adirondack chairs are positioned near a fire pit, which has gentle smoke rising. A picnic table rests nearby, providing a comfortable outdoor gathering space with views of the natural landscape.

Tiny home in Hartland

4.94 out of 5 average rating, 302 reviews

Private Modern Cabin w/View of Fields, Hills

Enjoy a modern private cabin in the heart of Vermont's pastoral Upper Valley Region. Combining "Glamping" with the comforts of a permanent structure, the "HakuBox" (Haku means "to exhale") was designed to sit lightly on the land and offer a simple, restorative experience. Note: no shower, but swimming holes nearby! Queen bed, fire pit w/grill, free firewood, Adirondack chairs, picnic table, free coffee & tea, dog-friendly with cable trolley, food & water bowls. $39 pet fee applies.

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, 677 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. We are as close or as far away as you would like us to be with our house right next door.

Top guest favorite

The private guest house is surrounded by lush greenery, featuring a covered porch with a chimney and hanging planters. A well-maintained lawn leads to the house, while a backdrop of rolling hills enhances the tranquil setting.

Cottage in Windsor

4.97 out of 5 average rating, 401 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.

Top guest favorite

A charming cabin constructed from natural materials is nestled among lush trees in a forested area. Sunlight filters through the leaves, casting dappled shadows on the ground. The cabin features large windows that invite the surrounding greenery inside.

Tiny home in Hartland

4.97 out of 5 average rating, 210 reviews

Cabin on the Hill

Enjoy a stay in the hills of Vermont - glamping at its finest! A 5-10 minute hike UPhill to a secluded getaway in the heart of Vermont. Amenities include a quaint outhouse, a unique outdoor shower, a 2 burner outdoor gas stovetop and a fire pit to roast marshmallows. The 12x14 screened in cabin with ladder accessed loft sleeps 2 comfortably. Don't worry about bringing pots and pans - cabin is equipped with dishes and a water supply. Adjustable LED lights to light up the night.

Guest favorite

The inviting bedroom features a queen-sized bed adorned with a colorful floral-patterned blanket. A gray sofa adds comfort alongside a small lamp and nightstand. Soft light fills the room, highlighting the vibrant green walls and decorative wall accents.

Guesthouse in Hartford

4.84 out of 5 average rating, 131 reviews

Addie's Place

A cozy and quiet space close to Dartmouth College (8 mins), Dartmouth Hitchcock Hospital (12 mins), and White River Junction Center (5 mins). You will have a private entrance to the space and access to a yard, a 3 season patio room, bedroom with a queen sized bed and queen pullout couch, a separate dining area, grill, and a private bathroom. There is no kitchen but there is a mini fridge, table, coffee/tea bar, plates, utensils, mugs, and a microwave.

Top guest favorite

Farm stay in Plainfield

4.97 out of 5 average rating, 243 reviews

Renovated 1817 Hobby Farm Close to Dartmouth

Come stay at PRIVATE GUEST QUARTERS on our hobby farm in Plainfield Village! Experience country living with a 20-minute proximity to Dartmouth University. You can see gorgeous views of Mount Ascutney from your window, hike to the French Ledges, visit St. Gaudens Park, or J.D. Sallingers farm. Every season is beautiful here! Or learn how to make macarons :) if you are brave enough.

Guest favorite

A small, wooden cabin is nestled on a grassy knoll, surrounded by trees. The cabin features a simple front door and a window, with a picnic table positioned nearby. The structure is elevated on stilts, providing an unobstructed view of the natural landscape.

Cabin in Royalton

4.92 out of 5 average rating, 183 reviews

Apple Hill Cabin at Four Springs Farm

Privately located walk-in camping sites are part of this beautiful working organic farm on a west-facing Vermont hillside. Guests will be dazzled by star-studded skies, treated to spectacular sunsets, and entertained by the two young farm cats. The farm is mosquito free but has millions of fireflies in summer. Have fun exploring. It's nature's playground at her best!!!

Top guest favorite

A charming treehouse is elevated on stilts amidst a forest of autumn foliage. A wooden staircase leads to the entrance, and a hammock is displayed on the deck, surrounded by colorful garlands. The ground is covered in crisp, fallen leaves.

Treehouse in Hartland

4.98 out of 5 average rating, 118 reviews

Lovely Treehouse Stay at Wise Pines- NoBo

Wise Pines is a Holistic & Sustainable Inn/Hiker Hostel that offers a unique farm experience. Reconnect with nature at this bedroom on stilts allows you to sleep amongst the trees peacefully. Farm stand food is available seasonally and yoga is available upon request. Explore 40 acres of walking trails through the woods, garden and around a tranquil pond.