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Family-friendly holiday rentals in Woodford

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Woodford

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

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Guest favourite
A log-sided cabin is surrounded by lush greenery under a clear blue sky. The structure features a distinctive half-moon window and a green metal roof. A spacious deck with outdoor seating and an umbrella is visible, inviting relaxation in a natural setting.
Cabin in Woodford

Lakeview Cabin in the Mountains - beautiful

Lovely log sided cabin situated across from Woodford lake with view. Large Great room cathedral ceiling, halfmoon window, pine ceiling & floors, dining table,woodstove, corner gas fireplace, full kitchen. Beautiful ambiance, rustic yet elegant. 3 bedrooms, full bath with clawfoot tub, romantic sleeping loft w sitting area. Basement play area heated with 2 beds for children. Central heat, washer/dryer TV/Roku, ceiling fans. Great getaway for nature lovers, skiers, snowmobilers, hikers. Wifi.

FamilyKitchenLocation

4.9 out of 5 average rating, 161 reviews
Top Guest favourite
A chalet-style home is surrounded by lush greenery, featuring a large three-sided wrap-around deck. Tall windows dominate the front, allowing ample natural light. To the side, a wooden garage complements the main structure, set against a backdrop of trees and an expansive lawn.
Chalet in Stamford

Peaceful VT Chalet w/ Mountain View’s

Our Peaceful chalet has everything you need. A fully equipped kitchen, 3 bedrooms, 2.5 baths, 2 living rooms, elec heat fireplace, outdoor fire pit, washer, dryer, Roku TV’s, great fiber optic internet. Accessible ATV/ snowmobile trails from property. 20 miles to Mt. Snow. Short driving distance to popular golf courses, shops, restaurants,breweries, kayaking, fishing, hiking, white water rafting ect An ideal base to explore the Green Moutain National Forests (VT) or the Berkshire Mountains (MA).

Indoor spacesKitchenBackyard

4.94 out of 5 average rating, 132 reviews
Top Guest favourite
A charming cottage is set in a green, open yard, surrounded by tall trees. A white fence encloses the property, with a small flowerbed in front. A rustic red barn is visible in the background, complementing the tranquil rural setting.
Farm stay in Bennington

The Farm Cottage- Quiet 1BR on Hobby Farm

Welcome to our peaceful 1-bedroom cottage on a small hobby farm, perfect for couples or solo travelers visiting the Bennington area. This cozy space is designed for rest and simplicity. Whether you're in town visiting family, exploring local trails, or just passing through for a few days, you’ll have a comfortable place to unwind and recharge. Thoughtful touches like fresh eggs from our chickens and homemade jams await you, while the cozy setup makes it easy to settle in and feel at home.

FamilyIndoor spacesBackyard

4.98 out of 5 average rating, 258 reviews
Top Guest favourite
A cozy living room features a brick fireplace as a central focal point, complemented by colorful seating arrangements on a warm-toned floor. A small table with a decorative tablecloth displays a notepad and pine cones. Natural light streams through large windows, creating a welcoming ambiance.
Home in Shaftsbury

Quaint One-Story Vermont House with Mountain View

From our quaint one-story house, you can see a variety of scenery, from the bright changing colors of the leaves in the autumn to the soft piles of snow in the winter. Experience the quiet of the nearby woods, and see roaming animals such as deer or turkey. Make sure to stop at one of the nearby lakes, each of which offers a variety of amenities, and lush scenery. In the winter, keep warm in the cozy living room next to the fireplace, while having a chat with your friends and family.

FamilyKitchenBackyard

4.88 out of 5 average rating, 154 reviews
Guest favourite
A cozy living area features a gray sofa and a matching chair beside a wooden coffee table. A stone fireplace is centered on the wall, with a television mounted above. Shelves display books and decorative items, while plants add a touch of greenery.
Cabin in Woodford

Charming Cabin with 2 baths in the Green Mountains

A cozy cabin nestled high up in the green mountains. A perfect getaway on a quiet street. This home is located up on Woodford Mountain. Across the street from Prospect Mountain (cross-country skiing and snow shoeing) and about 25-30 minutes to Mount Snow (downhill skiing). Vast snowmobile trail nearby. Visit the quaint general store nearby or go hiking in Woodford National State Park. At 2,000 ft elevation, the stars are on stage when it's a clear night.

FamilyKitchenBackyard

4.95 out of 5 average rating, 129 reviews
Top Guest favourite
The historic Gate House is framed by lush greenery and a manicured lawn, set against a vibrant sunset sky. Its stone façade and charming architecture are accentuated by soft lighting that bathes the exterior in warmth, inviting guests to explore the expansive outdoor space.
Home in Bennington

The Gate House--Experience Vermont!

The Gate House is a historic property located at the foothills of Mt Anthony. Built in 1865, the original structure of the house served as the gate house to the Colgate Estate, one of the most beautiful properties in Southwestern Vermont. Our home is just a few short miles to downtown where you can find local restaurants and breweries. We are not far from some of the best skiing/riding in the Northeast at Mt Snow, Bromley, Stratton and Prospect Mountains.

Indoor spacesFamilyBathroom

4.98 out of 5 average rating, 165 reviews
Top Guest favourite
A living area features a stone fireplace with a roaring fire, surrounded by large windows that invite natural light. A circular coffee table rests on a textured rug, while comfortable seating options include an upholstered chair and wooden accent chairs, complemented by soft lighting.
Cottage in Bennington

Cozy, bright 3-bedroom Cottage with fireplace.

Cozy, spacious brook-side cottage with 3 bedrooms, 2 baths, fully-equipped kitchen, fireplace, and serene, 382-acre country setting. Colorful artwork, designer furnishings, and well-appointed kitchen and bathrooms will make you feel welcome and at home. Historic charm of Bennington ten minutes away. NYC (182 miles); Boston (118); Mt. Snow (32); Prospect Mountain (13). Close to MASS MoCA (22), Tanglewood (49) and Manchester outlets (32).

FamilyKitchenValue

4.98 out of 5 average rating, 123 reviews
Top Guest favourite
A white farmhouse with a spacious front porch features rocking chairs and a welcoming front yard. A friendly dog is seen sitting on the green grass, surrounded by autumn foliage. The structure's windows and a gabled roof enhance its charming exterior.
Home in Bennington

The Vermont Farmhouse|Hiking|Dog Trails|Village

The Luxury of Slowing Down — Vermont Style. Leave the rush behind and feel rested, reconnected and renewed at our dog-friendly, beautifully restored 1860s farmhouse. Wide-plank floors, sun-filled rooms and modern comforts create a warm, impeccably clean retreat. Walk across the road into 280 acres of peaceful Mile Around Woods trails, or stroll into historic North Bennington for cafés and shops. It's all right at your doorstep.

Indoor spacesFamilyOutdoor spaces

5.0 out of 5 average rating, 135 reviews
Guest favourite
Cabin in Woodford

400+ Airbnb Visits: Incredible Mountain Cabin

Our cabin is off the grid, NO running water (read this twice) or indoor bathroom, but it’s comfortable and has been enjoyed by 100’s of Airbnb travelers. There is electricity, but this cabin takes an adventurer in the winter months. Winter Stays take work! Don’t be surprised of shoveling and bringing in your gear! Our reviews speak for how great rental is for people, thank you for considering a stay at our cabin.

KitchenIndoor spacesQuiet

4.85 out of 5 average rating, 388 reviews
Top Guest favourite
A white farmhouse-style structure is set on a lush green hill, surrounded by a clear blue sky. The building features a gabled roof, multiple windows, and a small cupola. A neat lawn frames the house, emphasizing its inviting exterior.
Home in Bennington

Cozy Modern Sugar House with spectacular views.

This beautiful Vermont home sits on 25 acres with spectacular views. We moved this sugar house structure to this land and had an architect adapt it to its surroundings. It has three walls of windows that display the amazing views. The house is surrounded by Mount Anthony hiking trails and a gorgeous pond. The location is a 5 minute drive to town or a lovely 20 minute walk.

FamilyKitchenBackyard

4.99 out of 5 average rating, 353 reviews
Guest favourite
Yurt in Dover

Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger

Seven minutes from the Mount Snow lifts, this creekside yurt turns mountain days into sauna nights. Ski, hike or explore Southern Vermont, then soak in the private hot tub, heat up the cedar sauna and settle in by the wood stove. The soaring dome, pool table, PS5, stocked kitchen and pet-friendly setup make it an easy year-round base for couples, families and friends.

FamilyIndoor spacesNearby

4.92 out of 5 average rating, 131 reviews
Top Guest favourite
A herd of sheep stands in a grassy field, surrounded by a mix of bare trees and mountains in the background. The sheep's coats are predominantly white with subtle variations in shades. The landscape is open, with a scattered straw covering the ground and a cloudy sky overhead.
Farm stay in Bennington

White Rock Farm

White Rock Farm is a working sheep farm in Bennington VT, part of the scenic and historic Valley of Vermont and surrounded by the Green and Taconic Mountains. The farm is a place where successive generations have been stewards of its 295 acres. First established in 1828, today it remains a working farm that includes livestock, maple syrup, and timber production.

KitchenIndoor spacesAccuracy

4.98 out of 5 average rating, 139 reviews

Popular amenities for Woodford family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top Guest favourite
Chalet in Wilmington

Mt Snow Chalet: Peaceful Escape w/Hot Tub

FamilyKitchenBathroom

5.0 out of 5 average rating, 131 reviews
Top Guest favourite
Treehouse in Wilmington

Beautiful timber-frame treehouse

Indoor spacesKitchenHospitality

5.0 out of 5 average rating, 114 reviews
Superhost
A uniquely designed raised container home features multiple levels and large windows that offer expansive views of the surrounding landscape. The structure includes a covered outdoor area below, and the combination of dark wood and metal creates a striking exterior appearance.
Shipping container in Whitingham

The House of Pi

Indoor spacesKitchenAccuracy

4.88 out of 5 average rating, 121 reviews
Top Guest favourite
Cabin in Wilmington

Mid-mod VT Dream Chalet near skiing, lake & forest

KitchenIndoor spacesAccess

5.0 out of 5 average rating, 135 reviews
Top Guest favourite
An inviting outdoor space features colorful chairs surrounding a fire pit, set against a winter backdrop. A cozy seating area on a deck showcases modern decor, including a patterned throw and a view of rolling hills framed by an oversized circular window.
Cottage in Shaftsbury

Schoolhouse Spa Retreat on a Vermont Farm

Indoor spacesKitchenHot tub

4.98 out of 5 average rating, 782 reviews
Top Guest favourite
Cabin in East Nassau

Fall Foliage Luxury Cabin & View Autumn Adventures

Indoor spacesFamilyCheck-in

4.97 out of 5 average rating, 107 reviews
Guest favourite
The inviting living room features a modern wood-burning stove against a backdrop of light wooden walls. A comfortable dark sofa is arranged around a round wooden coffee table, complemented by a decorative plant. Natural light filters through the windows, enhancing the cozy atmosphere.
Cabin in Londonderry

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba

Indoor spacesKitchenOutdoor spaces

4.95 out of 5 average rating, 267 reviews
Guest favourite
A large outdoor pool is surrounded by a wooden deck with lounge chairs and umbrellas. The background features a multi-story building with expansive windows. Vibrant autumn trees with colorful foliage frame the scene, providing a serene and inviting atmosphere.
Home in Wilmington

Cozy 4BR Cabin | Pools & Hot Tub | Near Mt Snow

KitchenFamilyView

4.89 out of 5 average rating, 180 reviews

Family- and pet-friendly home rentals

Top Guest favourite
A light-filled kitchen features modern appliances, including a vintage-style refrigerator. White cabinetry complements a wooden countertop. The open layout connects to a living area, where a cozy blue chair adds a pop of color. Large windows allow natural light to brighten the space.
Guesthouse in Bennington

Guest Cottage - Mountain Views, History & Hiking

FamilyKitchenBackyard

4.99 out of 5 average rating, 100 reviews
Top Guest favourite
The A-frame house is framed by tall trees, featuring large triangular windows that enhance natural light. A wooden deck extends to a seating area with two rocking chairs and a picnic table. A person walks their dog along the path leading to the entrance.
Place to stay in Stratton

The Chal-A-Frame Vermont

FamilyIndoor spacesPets

4.99 out of 5 average rating, 220 reviews
Top Guest favourite
Guesthouse in North Adams

Netherwood - North Adams Guest House with Views

FamilyIndoor spacesBathroom

5.0 out of 5 average rating, 336 reviews
Guest favourite
The unique dome-shaped structure is composed of iron and cement, surrounded by lush greenery. Large windows create a bright and airy atmosphere, while the greenhouse-style addition at the front enhances the connection to nature.
Dome in Bennington

5BR Rustic Mountain Sanctuary Dome Home

Indoor spacesFamilyTV

4.93 out of 5 average rating, 137 reviews
Guest favourite
An open living space features high, wooden beams and rustic decor, emphasizing cozy seating arrangements with leather couches. A large American flag hangs prominently on the wall, while a staircase leads to an upper loft area. Natural light filters through windows, illuminating the warm wooden interior.
Home in Shaftsbury

Stylish VT Barn+Guest Fall Favorite+Rare Find

FamilyKitchenHeating

4.91 out of 5 average rating, 128 reviews
Guest favourite
A stationary white bus sits on a gravel path surrounded by green grass. In the background, sparse trees and expansive fields are visible. Two outdoor chairs and a small shed can be seen nearby, highlighting the serene, rural setting.
Bus in Granville

Serene Bus Getaway Among Rolling Farm Land

KitchenIndoor spacesCheck-in

4.89 out of 5 average rating, 217 reviews
Top Guest favourite
The entryway features a welcoming entrance with a wooden door, adorned with a green wreath. A glimpse into the bright interior reveals modern seating and natural light streaming through large windows, enhancing the inviting space that awaits inside.
Chalet in Wilmington

Snug Chalet - Wi-Fi + Close to Mount Snow

KitchenFamilyAccuracy

4.97 out of 5 average rating, 146 reviews
Guest favourite
A serene path meanders through lush green grass, leading to a charming farmhouse surrounded by trees. The clear blue sky and gentle clouds create a peaceful backdrop, enhancing the natural setting of the property.
Home in Whitingham

Vermont lake house near Mt. Snow-fab 360 views!

Indoor spacesKitchenWalkability

4.92 out of 5 average rating, 119 reviews

Family-friendly home rentals with a pool

Top Guest favourite
A red wooden cabin nestled among trees, showcasing a welcoming front porch. Air conditioning units are situated to the side. Natural light filters through the foliage, creating a serene and shaded outdoor atmosphere.
Barn in Newfane

Beautiful rustic woods and fields retreat.

KitchenIndoor spacesAmenities

4.98 out of 5 average rating, 178 reviews
Top Guest favourite
The classic two-story farmhouse features white siding with black shutters. A green door welcomes visitors, while lush greenery and blooming lilac bushes create a natural frame. The surrounding lawn is expansive, emphasizing the peaceful rural setting.
Home in Salem

Historic Farm Stay | Heated Pool + Hot Tub

KitchenIndoor spacesSkiing

4.98 out of 5 average rating, 213 reviews
Top Guest favourite
A clear view of a fenced swimming pool is surrounded by lush greenery and trees. A stone pathway leads to the pool area, with well-maintained flower beds in the foreground. Seating options are available near the pool for relaxation.
Cottage in Averill Park

Cozy cottage with pool, walking distance to lake

FamilyIndoor spacesCleanliness

4.95 out of 5 average rating, 170 reviews
Superhost
A classic farmhouse is set against a backdrop of lush greenery, featuring a well-maintained exterior and welcoming front porch. Surrounding the home is an expansive lawn, with trees providing natural shade and enhancing the serene outdoor environment.
Home in Saratoga Springs

Town & Country Getaway: Pool Gardens Views 6 Acres

Indoor spacesFamilyBreakfast

4.83 out of 5 average rating, 206 reviews
Guest favourite
A charming red cabin is nestled among lush green trees, surrounded by moss-covered ground. The exterior features multiple windows, allowing natural light to fill the space. A small shed is visible to the left of the cabin, enhancing the serene woodland setting.
Cabin in Guilford

Silver Brook Cabin

KitchenIndoor spacesCleanliness

4.95 out of 5 average rating, 180 reviews
Top Guest favourite
An aerial view of the property showcases a spacious backyard featuring an in-ground pool, accompanied by a hot tub and lounge seating. The home, surrounded by lush greenery, displays a charming exterior with multiple windows and patio space, ideal for outdoor relaxation.
Home in Saratoga Springs

10 Min to Saratoga Track-Pool, Hot Tub, Game Room

KitchenIndoor spacesQuiet

5.0 out of 5 average rating, 102 reviews
Top Guest favourite
A spacious family room features a vaulted ceiling with wooden beams. Seating includes a sectional sofa and two lounge chairs. A large smart TV is mounted above a minimalist fireplace. Natural light floods in from the expansive glass doors leading to a balcony.
Cottage in Wardsboro

Modern Cottage between Stratton and Mount Snow VT

KitchenIndoor spacesCondition

4.97 out of 5 average rating, 113 reviews
Guest favourite
A rustic log cabin is set amidst lush greenery, framed by tall trees. A covered porch extends along the front, providing space for seating. Natural stone steps lead up to the entrance, and a small fire pit is visible in the foreground, surrounded by stones.
Cabin in Wardsboro

Leonard’s Log - Private Hot Tub, Fire Pit, A/C

Indoor spacesFamilyHeating

4.92 out of 5 average rating, 223 reviews

Destinations to explore