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Family-friendly vacation 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.

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Top guest favourite
Guest suite in Stockbridge
5 out of 5 average rating, 105 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.

Top guest favourite
A round yurt is surrounded by lush green trees, with a tan conical roof and large windows that invite natural light. The pathway leading to the entrance is bordered by various plants and shrubs, enhancing the connection to the natural setting.
Yurt in Bristol
4.92 out of 5 average rating, 346 reviews

Bristol Cozy Yurt near Hiking/Skiing|MapleFarm

Our cozy yurt is located within minutes of amazing, hiking, biking, skiing, breweries and much more! Relax around the fire while listening to our resident owls or stare up at the stars through the dome. We're centrally located to some of the best hiking and swimming skiing in Central Vermont. Mt Abe and Bartlett's Falls are the closest options. We're also close to civilization with several towns close by to explore for food, drink, art, and shopping. Or travel a bit further to Burlington..

Guest favourite
An A-frame chalet features a sloped metal roof and wooden exterior, surrounded by verdant greenery. A welcoming wooden deck with stairs leads to the entrance, inviting guests to enjoy the natural setting. Large windows allow for sunlight to illuminate the space.
Chalet in Stockbridge
4.84 out of 5 average rating, 174 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.

Guest favourite
A charming farmhouse exterior is shown at night, with warm light glowing from multiple windows. The snowy landscape surrounding the house is accentuated by tall trees under a dark blue sky. The roof displays a gentle slope covered in a blanket of snow.
Home in Stockbridge
4.87 out of 5 average rating, 148 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
A yurt with a beige and red exterior is surrounded by lush greenery. A wooden deck leads to the entrance, with comfortable seating visible. The backdrop features trees and an open view of the hillside, illuminated by natural light under a clear blue sky.
Yurt in Randolph
4.99 out of 5 average rating, 152 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
A spacious outdoor deck features a mix of seating, including lounge chairs and a table set for two. String lights are elegantly draped above, providing a warm glow. Surrounding trees add to the natural setting, enhancing the peaceful atmosphere.
Cabin in Stockbridge
4.94 out of 5 average rating, 121 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.

Guest favourite
A newly built tiny cabin is nestled among lush green trees, accessed by a wooden deck leading to a cozy seating area. Natural stones and grass surround the cabin, enhancing its peaceful woodland setting, while warm lights add a welcoming touch.
Cabin in Pittsfield
4.98 out of 5 average rating, 174 reviews

Tiny Vermont Cabin!

Newly built tiny cabin in the woods of Vermont! Perfect for a quiet get away and close by outdoor fun! Killington and Pico Mountain is 15 minutes away! Sugarbush is 50 minute drive. Coming to Pittsfield for a wedding? Riverside Farm is only .7 of a mile down the road! MUST have AWD/4x4 for winter access on dirt road and driveway. Cozy up by the newly added propane fireplace with an easy click of a button! Come experience the winter beauty Vermont has to offer!

Guest favourite
A large house with a gray exterior features a welcoming front porch and a gabled roof. Surrounding greenery includes trees and flower bushes, creating a peaceful outdoor environment. The driveway is visible, leading to the house amid a spacious lawn.
Home in Bethel
4.87 out of 5 average rating, 172 reviews

Affordable, private, surrounded by flower gardens

Enjoy the summer in beautiful Vermont. The guest area is the entire main floor of a large house with my quiet second home above. Private entrance, 2 bedrooms, full bathroom with washer and dryer, speedy fiber optic internet. The open kitchen has full sized stove and fridge with good cookware and appliances, adjacent to a large open living area. On a paved scenic road. Go up to Silver Lake for a swim, head out on any of the back roads for a run or a ride.

Top guest favourite
A stone pathway is framed by lush greenery and garden beds leading to the entrance of the chalet. Soft lighting from lanterns illuminates the steps, creating a welcoming atmosphere as it transitions from the natural surroundings to the home's entrance.
Chalet in Stockbridge
4.97 out of 5 average rating, 144 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.

Top guest favourite
A spacious living area features a light grey sectional sofa with cozy throw pillows. Natural light floods in through large glass doors that open to the yard, while a modern ceiling fan hangs above. A rug defines the seating arrangement, and simple decor adds warmth.
Cabin in Rochester
4.95 out of 5 average rating, 487 reviews

Black haus: a hip, cool house hidden in a forest.

You’ll love our place because of the high ceilings, the rural location, the coziness and its sense of place in nature. Our place is great for couples and solo adventurers who enjoy their privacy, who want to get away from it all but be close enough to a more 'country-urban' vibe. There is a deck for sunning, quite a large front and back yard. A great kitchen for meals at home, a forest to explore and miles of trails to mountain bike or hike.

Guest favourite
An A-Frame chalet is partially covered in snow, surrounded by a winter landscape. Snowmobiles are parked in front, with a vehicle also snow-blanketed. The wooden balcony and large windows suggest a cozy interior, while the sloped roof reflects the seasonal setting.
Chalet in Stockbridge
4.79 out of 5 average rating, 112 reviews

"Swiss Charm"- A Beautiful Riverfront Chalet

Nestled comfortably on the banks of the Tweed River just 9 miles North of the Killington Access Road just off Rt. 100, "The Skiers Highway" with Direct Access to VAST Trails. A 2BR 1 BA A-Frame Chalet is the perfect Pet Friendly weekend getaway. Quaintly decorated and well stocked...This is truly a "Home Away From Home".

Top guest favourite
A view from the balcony showcases the surrounding landscape, highlighting green hills and clear blue skies. Two adjoining buildings are visible, featuring sloped roofs and a variety of architectural styles. The area appears tranquil, with open spaces and scattered trees enhancing the natural scenery.
Condo in Killington
4.95 out of 5 average rating, 186 reviews

Bright Ski on/off Condo Full Kitchen-Free Shuttle!

Updated Ski on/off at the base of Pico overlooking the mountain! FREE Shuttle to Killington right downstairs. Roll out of bed, walk to the lift and finally get first tracks! Or, let yourself relax and just watch those getting first tracks from the comfort of the private balcony overlooking the trails!

Popular amenities for Stockbridge family-friendly rentals

When is the best time to visit Stockbridge?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$571 CAD$560 CAD$539 CAD$407 CAD$389 CAD$421 CAD$427 CAD$417 CAD$414 CAD$431 CAD$417 CAD$560 CAD
Avg. temp-6 °C-5 °C0 °C8 °C15 °C20 °C22 °C21 °C17 °C10 °C4 °C-2 °C

Quick stats about vacation rentals that are family-friendly in Stockbridge

  • Total vacation rentals

    Explore 50 vacation rentals in Stockbridge

  • Nightly prices starting at

    Stockbridge vacation rentals start at $126 CAD per night before taxes and fees

  • Verified guest reviews

    Over 2,050 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    50 of Stockbridge vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Stockbridge rentals

  • 4.9 Average rating

    Stockbridge stays are highly rated by guests—averaging 4.9 out of 5!