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Family-friendly holiday rentals in Woodbury

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Woodbury

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

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Guest favourite
A white farmhouse is set against a clear blue sky, surrounded by lush greenery and large trees. A private pool reflects the house and trees, creating a serene outdoor space. A rustic barn can be seen in the background, indicating the property's charm.
Home in Plainfield

Mountain View Farmhouse w/ Orchard, Pool is Open!

This magical property is Vermont at its finest. Bring the whole family to this idyllic farmhouse with panoramic mountain views, large private pool, apple orchard, flower gardens, fire pit and much more. Be as free as you imagine on 14 private acres of lawn, perennial gardens, fruit trees and lush woods with a meandering stream. Let the kids swim in the pool all day while you read in the shade of old locust trees while taking in one of the best views in Vermont.Find us on insta: @upper_east_eden

KitchenIndoor spacesBathroom

4.82 out of 5 average rating, 149 reviews
Guest favourite
The exterior of the house is characterized by dark grey siding contrasted by bright turquoise trim. Two orange chairs are positioned on a stone patio area, accompanied by two decorative statues. Multiple windows provide natural light while showcasing an inviting entrance.
Home in Hardwick

Historic House in the Village of Hardwick

Rochester House is near restaurants, trails, family-friendly activities, and lake beaches. It's convenient to many destinations, including, Hill Farmstead, Caspian Lake (beach) and Craftsbury. A short walk to the Farmer's Market, grocery stores, and most village restaurants. Downtown is .7 miles, 15 min walk. This may be too far in winter. There is a city plowed sidewalk all the way during snow season if needed. House of Pizza is only 2 blocks. We are in the village, please respect neighbors.

FamilyIndoor spacesOutdoor spaces

4.86 out of 5 average rating, 159 reviews
Top Guest favourite
The farmhouse is displayed with a classic white exterior and a metal roof. A welcoming front porch is flanked by steps leading up to the entrance. Surrounding fields stretch into the distance beneath a clear blue sky, showcasing the home's peaceful rural setting.
Home in East Montpelier

The 1919 Mountain Farmhouse, new hot tub and patio

Welcome to your charming mountain getaway—The 1919 Mountain Farmhouse! Located just 10 minutes away from Montpelier and 40 from Stowe proper, this newly renovated 1919 farmhouse comfortably sleeps 8 and is the perfect choice for a relaxing stay. Nestled among quiet farmland, you and your guests will enjoy sipping coffee/wine on the back deck with full mountain views. After a fun day enjoying local trails, shops, mountains, and more—a table inside or outside awaits a meal to be shared with all.

FamilyKitchenHospitality

4.99 out of 5 average rating, 138 reviews
Top Guest favourite
Aerial view of the vibrant Vermont landscape, showcasing rolling hills adorned with a diverse palette of fall foliage. The rustic barn sits among expansive fields, framed by trees displaying bright autumn colors, with distant mountains in the background under a partly cloudy sky.
Barn in Morristown

200 acre Stowe area Bunkhouse.

Hello and welcome to our Red Road Farm 'Bunkhouse' -- We're so happy to host you! Sitting on our 200 acre estate this authentic barn offers our guests a chance to relax in the beautiful rolling hills of Vermont. Access the vast majority of our historic Stowe area land -- from our apple orchards to our extensive walking paths in fields and woodland. We hope that you can experience such fun and quiet time in our cozy, western-style bunk room. Located only a 10 minute drive from downtown Stowe.

FamilyKitchenCleanliness

4.97 out of 5 average rating, 244 reviews
Top Guest favourite
A charming treehouse is nestled among lush green trees, featuring large windows that glow warmly at dusk. A connecting bridge is illuminated with string lights, creating a welcoming pathway. Ferns and forest foliage add to the natural surroundings, enhancing the serene woodland atmosphere.
Treehouse in Moretown

Treehouse at Bliss Ridge Farm - Best Views in VT!

This treehouse, the Birds Nest, is open May-Oct. Our “4-Season Treehouse @ Bliss Ridge,” is open year-round: https://www.airbnb.com/h/bigtreehouseatblissridgefarm — NEW SAUNA on property! Dr. Seuss-inspired tree home perched @top of 88-acre, organic hill farm, surrounded by 1000s acres of wilderness. Designed by B'fer Roth, DIY network host of The Treehouse Guys - built WITHIN living trees, not stilts! Private hiking & panoramic views of Worcester range, MR valley! No pets or animals please.

Indoor spacesKitchenHiking

4.97 out of 5 average rating, 202 reviews
Guest favourite
The exterior of a rustic log cabin is featured, showcasing a welcoming porch adorned with hanging plants and ambient lighting. A firepit surrounded by adirondack chairs invites relaxation. A grassy area leads to the wooden deck, with a view of the sky transitioning to evening hues.
Cabin in Wolcott

Cozy Log Cabin - Sauna - Fireplace - Sleeps 10!

Escape to a classic Vermont log cabin in charming Elmore—just 25 minutes from Stowe and Montpelier, without the traffic! Cozy up by the fireplace, recharge in the infrared sauna, cook in the fully stocked kitchen, or enjoy games, toys, and a fire pit under the stars. With comfy beds, AC, WiFi, and plenty of space for kids (and pups 🐾), it’s the perfect family-friendly retreat year-round. Easy access to Stowe, Smugglers Notch, Morrisville, & Montpelier. Lake Elmore is just minutes away!

Indoor spacesFamilyComfort

4.93 out of 5 average rating, 157 reviews
Guest favourite
Cabin in Calais

Fabulous Fall Foliage on water in the heart of VT

Welcome to Maple Corner! Come relax in this lakeside 4-season cabin tucked away in the heart of beautiful Vermont. This rustic but finished cabin features a full kitchen and all amenities you might need for a peaceful getaway. The wide deck overlooking Curtis Pond is the perfect place to have breakfast or listen to the evening loons calling. Swim in the summer, snowshoe or ski in the winter. Walk to the country store or visit Montpelier 15 minutes away for more activities. Come escape!

Indoor spacesFamilyValue

4.87 out of 5 average rating, 124 reviews
Top Guest favourite
A wooden bridge leads to the entrance of the treehouse, surrounded by trees displaying autumn colors. The structure features large windows and a unique architectural design, blending nature with handcrafted elements.
Treehouse in Waterbury

The Roost - Recharge & Relax

Enjoy being immersed in nature when you stay in this unique treehouse to unwind while experiencing some of the best sights and nature in Vermont. This cabin up on stilts and bordering one of Vermont's beautiful state parks. Views of the walkable Waterbury reservoir can be seen from its perch in the trees. "The Roost" aims for a balance of rustic meets elegance. With a tiled shower and heated flooring through out- one can truly reconnect and recharge in this unique experience.

Indoor spacesKitchenHot tub

4.94 out of 5 average rating, 194 reviews
Top Guest favourite
A rustic cabin with a wooden exterior is surrounded by lush greenery. The inviting porch features several rocking chairs and is accessed by steps from a grassy area, while a gravel driveway leads to the entrance, enhancing the private setting.
Cabin in Wolcott

Meadow Woods Cabin, private, cozy and unconnected

Enjoy beautiful sunsets from your rocking chair on the cabin's wonderful porch. There is a large, well equipped kitchen, open space floor plan, new shower unit and plenty of closet space in the bedroom. Easy access to VAST snowmobile trails, within an hour's drive to 3 ski areas (Stowe, Smuggler's Notch and Jay Peak), X-Country skiing right outside the door or in Craftsbury or Stowe. Elmore State Park is 3 miles away. Hiking trails and kayaking abound!

FamilyKitchenComfort

5.0 out of 5 average rating, 177 reviews
Top Guest favourite
The house is set against a backdrop of vibrant fall foliage, with a blend of yellow and red leaves surrounding it. Large windows reflect the colors of the trees, while the modern architecture adds to its charm. The scene conveys a harmonious connection with nature.
Home in Stowe

Spacious Eco-Friendly Stowe Home for Family Fun

Vacation/Work Remotely or both in this 5 BR and 5 BA gorgeous mountain eco-friendly home. FIBER 100 meg symmetrical wifi, a quiet workspace with desk, monitor, and printer. Fully stocked kitchen, ping pong, fire pit, large family space but quiet spaces too, and 3 ensuite bedrooms! Conveniently located close to town and a short drive to skiing. This is a great family space to reconnect or a space to work remotely for a change of pace.

KitchenIndoor spacesComfort

4.98 out of 5 average rating, 203 reviews
Superhost
A farmhouse is positioned in a scenic landscape, with a gravel driveway lined by greenery leading towards it. The sunrise casts warm tones across the sky, reflecting on puddles in the foreground, while a distant tree stands amidst the open fields.
Farm stay in Elmore

Cozy rustic Cottage // Close to Stowe

Beer, cheese, long walks in the woods & skiing! Our 180 year old little Farmhouse is close to all the rural essentials. Set on bucolic backroads, looking out towards Stowe, the little Farmhouse is a Vermont country paradise. Starting in 2026, we will be building a home adjacent to the farmhouse. The property will be a bit of a construction project through the Summer. *Read the “rules” section if you plan to bring a dog :) .

KitchenIndoor spacesHospitality

4.96 out of 5 average rating, 372 reviews
Top Guest favourite
Tiny home in Wolcott

The Caterpillar House: Tiny w/ Hot Tub & Fire Pit

Escape to our charming tiny house—The Caterpillar House—where comfort meets minimalist living in scenic Elmore, Vermont. Ideal for solo travelers, couples, or small families seeking a peaceful retreat. Enjoy a private hot tub, fire pit under the stars, and direct snowmobile trail access—perfect for summer and winter getaways. Located on our shared property, this cozy haven is surrounded by nature for a truly relaxing stay.

KitchenIndoor spacesAccuracy

4.98 out of 5 average rating, 228 reviews

Popular amenities for Woodbury family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favourite
A modern treehouse features a warm wooden exterior, elevated on a platform among vibrant autumn foliage. Large glass windows provide a view into the inviting interior space. Steps and a small deck lead to seating arranged on the ground level, surrounded by natural scenery.
Treehouse in Newport

Secluded Luxury Treehouse - Hot Tub + Projector

Indoor spacesFamilyAir conditioning

4.97 out of 5 average rating, 335 reviews
Top Guest favourite
Cabin in Morristown

Modern Post&Beam w/ Hot Tub, Waterfall, Mtn. Views

KitchenFamilyHospitality

4.97 out of 5 average rating, 185 reviews
Top Guest favourite
The rustic treehouse, set amidst towering trees, features a wooden deck leading to the entrance. Warm lighting illuminates the inviting exterior, while a hot tub is positioned nearby. The tranquil setting offers views of the water, blending nature with cozy accommodation.
Treehouse in Newport

Vermont Treehouse with Hot Tub — Open All Winter

Indoor spacesKitchenHot tub

4.99 out of 5 average rating, 944 reviews
Guest favourite
An outdoor deck is equipped with a dining table and chairs, overlooking a vibrant landscape of fall foliage in various shades of red, orange, and yellow. A hot tub is positioned nearby, providing views of the surrounding trees and mountains.
Cabin in Morristown

Stowe Sky Retreat: Hot Tub/Views/Family Friendly

KitchenFamilySkiing

4.94 out of 5 average rating, 179 reviews
Top Guest favourite
An aerial view captures a modern farmhouse-style condo surrounded by trees with vibrant autumn foliage. The property features a wide deck, outdoor space, and a gazebo to the side, complemented by a manicured lawn and gravel pathway leading to the entrance.
Condo in Stowe

Renovated 4BD House: Hot Tub, Sauna & Backyard

Indoor spacesKitchenOutdoor spaces

4.97 out of 5 average rating, 158 reviews
Guest favourite
The A-frame treehouse is illuminated by warm string lights, showcasing a spacious deck above the ground. The structure is nestled among trees, featuring a mix of wooden materials and large windows that highlight the inviting interior. A cozy seating area is visible on the deck.
Treehouse in Johnson

Designer A-Frame Treehouse | Hot Tub & Sauna

KitchenFamilyRiver

4.92 out of 5 average rating, 105 reviews
Guest favourite
The spacious living area features a unique wooden coffee table, complemented by a light-colored sectional sofa. Large windows along the slanted walls allow natural light to fill the space, while potted plants and decorative elements enhance the inviting ambiance.
Cabin in Stowe

The Canopy House—Remodeled Vermont A-Frame Near Downtown

Indoor spacesKitchenComfort

4.92 out of 5 average rating, 420 reviews
Guest favourite
An outdoor area features a spacious flagstone patio with a large hot tub and seating options. Surrounding greenery provides a natural backdrop, while distant mountains can be seen under a partly cloudy sky. Potted plants add a touch of color to the setting.
Chalet in Stowe

Contemporary Chalet in Stowe

KitchenIndoor spacesLaundry

4.95 out of 5 average rating, 402 reviews

Family- and pet-friendly home rentals

Top Guest favourite
The red wooden house features a welcoming entryway with a prominent front door framed by large windows. Bright green foliage lines the path, enhancing the natural setting. The garage is visible on the left, with sunlight illuminating the exterior.
Home in Hyde Park

CLASSIC VT STYLE

Indoor spacesKitchenLayout

4.97 out of 5 average rating, 303 reviews
Top Guest favourite
A spacious lodge architectural design features wooden logs and multiple levels. Balconies adorn the upper floors, and warm lights emanate from the windows, giving a welcoming appearance. Firewood is stacked nearby, and a well-maintained yard is visible with greenery and flowers in bloom.
Farm stay in Danville

Curtis Vance Memorial Orchard

FamilyKitchenTV

4.92 out of 5 average rating, 200 reviews
Top Guest favourite
An upstairs room features a spacious bed dressed with soft linens and a colorful decorative pillow. A cozy seating area is provided by a couch and a rocking chair. A patterned rug adds warmth, while natural light filters through multiple windows.
Cabin in Hyde Park

Dream Cabin in Vermont

KitchenIndoor spacesComfort

4.94 out of 5 average rating, 618 reviews
Guest favourite
A charming red cottage exterior features white shutters and a welcoming porch. A red bench is positioned to the left of the entrance, surrounded by blooming flowers. The door is framed by a screen, and a grassy field extends in the background.
Guesthouse in Hyde Park

2 bedroom cottage at Stony Brook Farm- Stowe area

KitchenIndoor spacesNearby

4.92 out of 5 average rating, 477 reviews
Top Guest favourite
The log cabin features a charming exterior with a prominent stone chimney and rustic red accents. It is surrounded by lush greenery and tall trees, with a serene yard that conveys a peaceful retreat in nature. A welcoming wreath adorns the front door.
Cabin in Stowe

Charming log cabin w/ fireplace in Stowe village

KitchenFamilyParking

4.97 out of 5 average rating, 261 reviews
Guest favourite
The cottage is nestled among trees, positioned on a gentle slope beside a flowing brook. A wrap-around deck extends from the structure, providing views of the surrounding nature. The peaceful sounds of water accompany the serene atmosphere created by the lush greenery.
Cottage in Morristown

The Cottage on Sterling Brook

KitchenIndoor spacesRiver

4.92 out of 5 average rating, 117 reviews
Top Guest favourite
A rustic cabin with a red wooden exterior is situated at the lake's edge, surrounded by dense greenery. A deck extends from the cabin over the water, while mist rises from the serene lake's surface, creating a tranquil atmosphere.
Cabin in Wolcott

Boathouse Cabin on Lake Wapanacki with Sunset View

Indoor spacesKitchenWi-Fi

4.97 out of 5 average rating, 232 reviews
Guest favourite
A cozy cabin nestled among trees features a wooden exterior and a vibrant red metal roof. A spacious porch wraps around the front, bordered by greenery. Sunlight filters through the leaves, creating a serene and inviting setting in a natural woodland environment.
Cabin in Morristown

Birch Tree Cabin! Pets Welcome

Indoor spacesKitchenCondition

4.91 out of 5 average rating, 278 reviews

Family-friendly home rentals with a pool

Guest favourite
A cozy living area features a built-in conversation pit surrounding a modern fireplace. Natural light streams in from large windows, illuminating comfortable seating adorned with colorful cushions. Wooden bookshelves filled with books create a warm and inviting backdrop.
Townhouse in Stowe

Ski In Ski Out, Chic, Fun, Cozy, Grt Location!

FamilyKitchenAccess

4.94 out of 5 average rating, 158 reviews
Guest favourite
A private outdoor area showcases a swimming pool with a colorful floating toy. The pool is surrounded by a wooden deck and features lounge chairs. In the background, a light gray house with a porch and seating areas is visible, framed by mature trees and shrubs.
Apartment in Williamstown

Cozy/Private, close to hospital, i-89

Indoor spacesKitchenCondition

4.91 out of 5 average rating, 185 reviews
Top Guest favourite
A red-painted two-story house is framed by lush green grass and colorful flower beds. A welcoming porch features two white chairs and wooden barrels. A friendly dog is seated at the entrance, adding a homely touch to the exterior.
Place to stay in Johnson

Château Chavis

FamilyIndoor spacesOutdoor spaces

4.98 out of 5 average rating, 185 reviews
Top Guest favourite
A spacious two-story home is set among lush greenery, with a large front deck featuring white railings. The exterior showcases a mix of light-colored siding and dark shutters, while tall trees provide a natural backdrop, creating a peaceful atmosphere.
Home in Stowe

EPIC Stowe Getaway - Great For Families & Friends

KitchenIndoor spacesOutdoor spaces

4.98 out of 5 average rating, 313 reviews
Top Guest favourite
The heated in-ground pool is framed by a spacious patio, showcasing a view of the Richelieu River at sunset. Lush greenery surrounds the area, with a fence enhancing privacy. Comfortable seating arrangements are present near the pool, creating a welcoming outdoor space for relaxation.
Cottage in Noyan, Quebec

Sunset Cottage on the Richelieu River CITQ#302701

KitchenIndoor spacesOutdoor spaces

4.98 out of 5 average rating, 330 reviews
Top Guest favourite
The exterior of a red house is surrounded by lush greenery and a variety of plants. A covered porch with wooden beams adds charm, while the expansive lawn invites leisurely outdoor activities.
Farm stay in Saint-Ignace-de-Stanbridge

The Gîte des Sœurs Racines

Indoor spacesFamilyCheck-in

4.98 out of 5 average rating, 106 reviews
Guest favourite
Townhouse in Lincoln

Loon Views · 3BR King + Bunkroom

FamilyIndoor spacesCondition

5.0 out of 5 average rating, 146 reviews
Guest favourite
A hot tub is situated beneath a covered gazebo, surrounded by natural foliage. A pathway leads through decorative stones to a cedar sauna in the background, while a gentle mist rises from the hot tub, creating a serene atmosphere.
Chalet in Mansonville

Chalet Potton Cottage - spa, sauna & pool

KitchenFamilyBathroom

4.86 out of 5 average rating, 415 reviews

Destinations to explore