Family-friendly holiday rentals in Stockbridge

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Stockbridge

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

0 of 0 items showing

1 of 3 pages

Guest favourite

Yurt in Randolph

4.93 out of 5 average rating, 210 reviews

Peaceful Woodland Yurt with Pond View

Enjoy the natural beauty of Vermont in this amazing, fully loaded, 14' guest yurt! It comes with a toasty propane fireplace, queen bed, two burner cooktop, fridge, great wi-fi, an incredibly charming and immaculate bathhouse, magnificent views, and privacy! This is the perfect getaway for those seeking peace and natural beauty without sacrificing comfort or amenities! Explore our remote hiking trails and beautiful pond. And be sure to enjoy off-grid meditation yurt when available in season.

Top guest favourite

Guest suite in Stockbridge

5 out of 5 average rating, 100 reviews

Studio Suite with Vermont Style & Amazing Views

Central to Killington, Pico & Sugarbush Ski Areas. Breathtaking views. Features all Vermont has to offer in any season - Golf, Downhill & X-country Skiing, nearby VAST trails, Snowshoeing, Hiking, Trail & Road Biking. Unit is en suite w/sitting area, dining table/desk, kitchenette (no stove). Shower and toilet with ADA bars. Handicap accessible. Large closet, dresser. Streaming TV/DVD/VHS, selection of games, discs and tapes. 2 entrances - public and private. Stone patio and fire pit. Quiet.

Guest favourite

Chalet in Stockbridge

4.92 out of 5 average rating, 183 reviews

Killington ski house winter MTbike -new jacuzzi

Killington Ski Area with access to snowmobile mountain biking trails. This 3 bedroom, 2 bath upper unit duplex. with outdoor private Jacuzzi open year round with barbecue on very nice decks for those nicer days , snow mobile right from the house , on the tweed valley vast trails , in the summer mountain bike on the green mountain trail system right on our mountain keep us in mind for the summer event like the spartan race and the peak series Mt biking events Fantastic unit check our reviews

Guest favourite

Guest suite in Barnard

4.87 out of 5 average rating, 152 reviews

Easy Peasy Studio - Barnard/Woodstock VT

A Vermont getaway in this spacious guest suite located downstairs of the event barn with private yoga studio. The suite has a hardwood, VT crafted, queen size bed, decent size kitchenette, TV, couch area, sitting desk & yoga props for your relaxing pleasure. Sleep in, take your time, no rush. Enjoy the grounds & sip coffee in the gardens. Revitalize & restore in a quintessential Vermont town surrounded by green mountains & silver lakes. This suite is a basement studio down flight of stairs.

Guest favourite

Treehouse in Stockbridge

4.93 out of 5 average rating, 123 reviews

Romantic Treehouse- Hot tub, A/C, 20 Min to KLT

New treehouse was built by me with my own two hands during the pandemic. The architect styled design is one of a kind with huge windows. Radiant Heat, custom bathroom/kitchen. My grandparents once owned and operated a dairy farm in the area and I want to share this treehouse and surrounding area with my guests. Ski or Ride in only 20 min to Killington and resorts. My treehouse is located on the historic ski highway with Killington-20 min, Pico, Okemo, Sugarbush, Saskadena Six, and Stowe.

Superhost

Chalet in Stockbridge

4.84 out of 5 average rating, 164 reviews

Vermont Chalet

Killington Skiing, Pico Peak, Sugar Bush, Mad River are all within distance. Killington is 14 miles away. Fall folliage is fabulous; kitchen well equipped; very light and lovingly cared for. Spring and summer are just as wonderful. I am walking distance to the White River where there is canoeing, tubing and swimming. Within walking distance is the Gaysville Campgrounds. Here you'll find river access to a fabulous swimming hole in the White River as well as trails to explore or walk your dog.

Top guest favourite

Apartment in Killington

4.99 out of 5 average rating, 103 reviews

Elegant Alpine Condo *Pool*

Newly renovated 1-bedroom Whiffletree condo with upscale alpine style, minutes from l bike park, adventure center, and golf course. Please note there is no air conditioning, but the cool mountain air and provided fans typically keep the space comfortable. Fully stocked with essentials and includes a locker for your gear. Relax and enjoy the onsite outdoor pool. Easy access to summer fun and scenic Vermont trails. Sleeps up to 4 with a king bed and queen pullout sofa. Killington Reg #007718

Superhost

Home in Stockbridge

4.87 out of 5 average rating, 146 reviews

Escape to Vermont

Welcome to the Red House at Stony Brook! This remodeled 1800's farmhouse offers peace, solitude and comfort in Vermont's national forest. Gaze at stars from the bedroom window and decompress in the mountains. Or, set out for a day of cycling, hiking, skiing and exploring all Vermont has to offer. A chance to experience wildlife, such as moose, birds, bears, turkeys and more. Nearby are Killington Mtn, Sugarbush, famous cycling roads, and several of VTs world renowned eateries and breweries.

Top guest favourite

Yurt in Randolph

5 out of 5 average rating, 140 reviews

Howling Wolf Farm Yurt--A Magical Glamping Retreat

Our 88-acre farm spreads up a steep hillside above the village of Randolph, one mile away. The land is a mixture of open areas where we rotate our sheep flock daily, and wooded land with trails and old stone walls. You might hear the occasional car or truck on a nearby road, but more likely you'll hear our sheep baaing to one another or the cows across the valley trumpeting, or the abundance of birdsong. The energy here is calming and peaceful--we know you will love it as much as we do.

Guest favourite

Cabin in Stockbridge

4.95 out of 5 average rating, 112 reviews

1958 Classic "Hunting Cabin" w/ Breathtaking Views

Welcome to CAMP TREETOPS, located in the heart of the beautiful Vermont mountains. Our cabin is nestled at the top of a private mountain, surrounded by breathtaking views of Killington, Pico mountains, and the White River. Originally purchased from a Sears & Roebuck catalog as a hunting cabin owned by the same family until 2019. The cabin has since been transformed into its original vintage classic camp décor with antique furnishings and unique vintage finds that take you back in time.

Top guest favourite

Tiny home in Hartland

4.97 out of 5 average rating, 202 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 favourite

Chalet in Stockbridge

4.96 out of 5 average rating, 132 reviews

Gnome Home Mountain Ski Chalet w/Sauna Killington

Mountaintop Chalet perched in the heart of Green Mountains. Enjoy true mountain living all year long 25m to Killington, White River access minutes from home, abundance of hiking trails, and golf courses. Central to Killington, Rochester, & Woodstock. After your adventures, return to a welcoming & comfortable home with beautiful views from every room, multiple decks, new! fireplace, & sauna, and plenty of special touches to help you unwind and relax.