Family-friendly vacation 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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Top guest favorite
Cabin in Shaftsbury
4.99 out of 5 average rating, 473 reviews

Vermont Dream Cabin~70 Acres w/Hot Tub & Fireplace

Log cabin w/ hot tub on 70 acres of Vermont forest with hiking/snowshoe trails, river & mountain stream. Cozy up with wine, games or book by the huge stone woodburning fireplace with fav music from the vintage Bose stereo, enjoy coffee & stargazing on the rocking porch while taking in the mountain views & wildlife or explore the forest & river trails. Enjoy making meals in the ample fully stocked kitchen, the outdoor grill & around the campfire. Crisp AC.*4x4/AWD a MUST for WINTER only BOOKINGS*

Guest favorite
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
4.91 out of 5 average rating, 159 reviews

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. 2 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.

Top guest favorite
Tiny home in Wilmington
4.99 out of 5 average rating, 378 reviews

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Guest favorite
A white two-story house sits at the intersection of a quiet street, surrounded by vibrant autumn foliage. A well-maintained yard features a mix of mature trees, with golden and orange leaves contrasting against the blue sky. A leaf-covered path leads toward the entrance.
Loft in Bennington
4.82 out of 5 average rating, 129 reviews

1 bedroom guest house on dead-end rd

Enjoy a peaceful and private space with 1 bedroom, 1 bath, full kitchen and on site parking. Last house on a dead end rd. 5 min from Southwestern VT Medical Center. 40 min from Mount Snow. 25 min from MassMoca. 15 min walk to Main St where you can enjoy great food and shops. No smoking on premises. Please note there is stairs separating the bedroom (downstairs) and living area, bathroom, and kitchen (upstairs). The stairs are steep and may be difficult for some people.

Guest favorite
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
4.95 out of 5 average rating, 129 reviews

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.

Top guest favorite
The cabin’s exterior is surrounded by trees, featuring a sloped roof and large glass doors that invite natural light. A spacious deck is furnished with multiple red tables and chairs, ideal for outdoor dining. A grill is positioned nearby, with a gravel pathway leading to the surroundings.
Cabin in Petersburgh
4.94 out of 5 average rating, 274 reviews

Cozy Retreat in the Trees

Time travel to 1958 in this architectural gem! This mid-century modern glass and wood cabin is 300 yards away from a charming small lake. The house is NOT on the lake itself, but it is surrounded by trees in a lovely secluded spot. The only heat is a wood stove... but there is a 4-person cedar barrel sauna in the woods that is electric. A classic 1952 Spartanette travel trailer serves as an extra bedroom. This is a true retreat for romance and adventure.

Top guest favorite
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
4.98 out of 5 average rating, 769 reviews

Schoolhouse Spa Retreat on a Vermont Farm

Escape to our historic and lovingly-renovated schoolhouse on a 250-acre verified-regenerative farm, where Green Mountain views meet modern comfort. Unwind in your private hot tub and barrel sauna after exploring farm trails, then fall asleep to the gentle sounds of sheep grazing in the pastures below. This is Vermont at its most authentic—working farm life with all the luxury. Level 2 EV charger, in-unit washer/dryer, and ductless AC for summer comfort.

Guest favorite
Cabin in Woodford
4.84 out of 5 average rating, 385 reviews

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.

Top guest favorite
Chalet in Wilmington
5 out of 5 average rating, 125 reviews

Mt Snow Chalet: Peaceful Escape w/Hot Tub

Escape to the serene beauty of Vermont's Green Mountains at the Mount Snow Chalet, a charming retreat nestled on a private wooded lot in the desirable Chimney Hill community of Wilmington. 🏠🌳 Just minutes from the slopes of Mount Snow, our chalet offers the perfect blend of rustic charm and modern amenities for an unforgettable getaway. Designed with love and care, we invite you to relax and stay awhile! 🥰

Guest favorite
The cabin exterior is visible, showcasing a two-story structure with horizontal siding. A spacious front deck is situated above a garage, and large windows offer natural light. Lush greenery surrounds the property, creating a secluded atmosphere in a wooded setting.
Cottage in Woodford
4.82 out of 5 average rating, 111 reviews

Love the outdoors? This is the place for you!

Cabin is a block up from "Big Pond" in the heart of the Green Mountains. Great for small or large guest count. Spring/Summer/Fall: Non-motorized watercraft lake access, hiking trails, golf, biking and many fairs & quaint stores to visit nearby. Winter: 30 minutes to Mount Snow, 5 minutes to Prospect Mountain & in the VAST snowmobile trail system. Family-owned for 3 decades with continuous updating.

Top guest favorite
Two wooden chairs are positioned on a grassy area, facing a gently sloping hill. A modern white farmhouse is visible alongside a deck with stairs. In the background, trees frame the serene landscape, and mountains are faintly visible under a cloudy sky.
Apartment in Bennington
4.92 out of 5 average rating, 197 reviews

Scenic Vermont Studio

This beautiful retreat is halfway between the ski slopes of southern Vermont and the cultural centers of Williamstown and North Adams, MA. The residence is a modern, spacious, basement apartment, part of an 1860 farm house. It has its own private entrance around the back of the house at ground level. Solar garden lights and motion detector lighting will illuminate your path to the apartment.

Top guest favorite
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
4.99 out of 5 average rating, 348 reviews

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.

Popular amenities for Woodford family-friendly rentals