Family-friendly holiday rentals in Dummerston

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Dummerston

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

1 of 1 pages1 / 1

Top guest favourite

Two white lounge chairs are positioned around a small black fire pit in a grassy area. Lush greenery and trees define the backdrop, while an open space creates a sense of privacy and tranquility.

Flat in Brattleboro

River View apartment

Beautiful completely furnished 1 bedroom apartment with a private driveway and deck. Less than a half hour from skiing and 5 min away from snowmobile trails. It is located along the west river where every summer you can go tubing, swimming, or kayaking. Across the river is a bike/walking path that leads right to the Marina restaurant on Putney Rd in Brattleboro. Bakery/café, Art Gallery and Retreat Farm all close by A gorgeous view of the river and mountain across the street .

4.99 out of 5 average rating, 201 reviews

Top guest favourite

Exposed wooden beams frame the room, complemented by warm brick walls. A cozy fireplace sits centered against the wall, with decorative art above it. A comfortable chair and lamp are positioned nearby, while a television and small dresser provide functional elements in the living space.

Cottage in Newfane

Cozy Vermont Antique Sugar House with Fireplace

Enjoy a peaceful and unique stay at this beautiful 1796 Sugar House. Luxury bedding, cozy fireplace, soaring timbers to a cathedral ceiling make this a special place. There is a Queen size bed on the main floor and twin beds in the sleeping loft accessible by a ladder. Try some of our wonderful local restaurants and shops. Lots of hiking trails to explore. Winter sports all around, or just enjoy some hot chocolate, a fire, and a good book. You are sure to enjoy the “Sugar House”.

4.99 out of 5 average rating, 297 reviews

Guest favourite

A spacious sleeping area features two large beds with soft linens, positioned under skylights that fill the room with natural light. Wood beams and a warm wood floor enhance the rustic charm, while large windows overlook the surrounding trees.

Flat in Dummerston

~Serene Barn Retreat~

Peaceful, romantic retreat in this stunningly large, 1850's remodeled barn apartment. The historic barn is nestled into hundrends of acres of Nature Conservency. Many old maple and pine trees, hiking trails and breathtaking views will welcome you along the the drive here. If you'd like to book a healing retreat I offer Reiki sessions to guests. Inquire when you book. *Mount Snow is 35 minutes away. Okemo, Stratton, Bromley and Magic is 1 hour away and Stratton is 1 hour away.

4.93 out of 5 average rating, 440 reviews

Top guest favourite

The house is illuminated at night, showcasing its welcoming exterior and solar panels. A fire pit filled with glowing embers sits in the foreground, complemented by two Adirondack chairs. The spacious patio area is visible, surrounded by a lush garden.

Home in Newfane

Peaceful cabin close to skiing & Brattleboro

Country privacy close to the best of Southern VT! This spacious home is close to skiing (20 min to Mt. Snow; 35 min to Stratton), river swimming holes, hiking, biking, art galleries and great restaurants. Open concept with fireplace, cook's kitchen, jet bathtub, gardens, winter hot tub off deck, and large patio and fire pit give the perfect vibes for your VT gathering. Secluded from neighbors but close to amenities, this home is a comfortable and peaceful retreat.

4.98 out of 5 average rating, 161 reviews

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.

Within the Fritz Conference Center, tucked into the beauty of the Vermont Countryside, is this charming apartment/ mini house. Part of a renovated 19th century barn it is the perfect getaway. It sits on over 33 acres of fields, woods, apple orchard and Mountain View’s. 2 miles from historic Newfane Vermont, you are able to enjoy privacy, while close to the many attractions of the area. We are also dog friendly. There is an extra fee of $50 per trip per dog

4.98 out of 5 average rating, 178 reviews

Guest favourite

Home in Dummerston

The Sugarhouse

The quintessential Vermont stay! The Sugarhouse is a fully furnished one bedroom cottage, formerly a working sugarhouse built in 1915 to house the boilers that converted raw sap to maple syrup. It is located on a quiet Vermont country road bordered by historic New England dry stone walls, maple trees, and the beautiful Scott Farm. While you’ll feel a world away, you’ll be only 5 miles from Interstate 91 and 10 minutes from Brattleboro or Putney.

4.96 out of 5 average rating, 133 reviews

Top guest favourite

The exterior of a renovated log cabin is presented, featuring a red metal roof and a charming porch with steps leading up. The cabin is surrounded by lush greenery, with rolling hills visible in the background under a clear blue sky.

Cabin in Newfane

Log Cabin: Amazing Views, River Frontage, Hot Tub

A sparkling clean, recently renovated log cabin in the woods with beautiful views of river and mountains. Located by the charming villages of Williamsville and Newfane, 12 miles from Mount Snow, and right on the crystal clear Rock River. It's the perfect place for a romantic getaway, a family vacation and quality times with good friends. Now also with outdoor hot tub with views of mountains, river and the wide, open sky above.

4.99 out of 5 average rating, 318 reviews

Guest favourite

The bedroom is designed with a spacious bed adorned with crisp white linens. A large triangular window provides a serene view of lush greenery outside, allowing natural light to fill the room.

Cabin in Townshend

Modern Cabin with Outdoor Spa on Vermont Farm

Romantic modern cabin with private hot tub on a 100-acre Vermont farm. This Scandinavian-style retreat features soaring windows, a king bed with luxury linens, a cozy fireplace, and a sleek kitchen. Perfect for couples seeking a peaceful getaway, farm stay, or eco-friendly escape. Soak under the stars, meet our friendly goats, and enjoy the beauty of southern Vermont from your light-filled solar-powered cabin.

4.96 out of 5 average rating, 205 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.

4.92 out of 5 average rating, 131 reviews

Top guest favourite

The exterior of the house is framed by lush greenery and trees. A gentle path leads to the front entrance, which is sheltered by a small porch. The metal roof and pastel siding complement the natural surroundings, creating a cozy and inviting facade.

Home in Putney

Cozy Train Depot in Putney Vermont

Charming and cozy 1 bedroom house in Putney, Vermont. A former train depot, this home is just a few minutes walk to the Connecticut River with boat launch for enjoying fishing, swimming, canoeing and kayaking. Or curl up in the window seat and enjoy the fire!

4.95 out of 5 average rating, 377 reviews

Top guest favourite

A charming wooden house is surrounded by a snowy landscape, showcasing a large deck and steps leading to the entrance. Snow-covered trees and a clear blue sky enhance the serene setting. The structure features multiple levels, presenting a cozy, inviting exterior.

Cottage in Newfane

Ridgeview: Cozy Cottage with a View

At "Ridgeview" you can go to sleep to the flicker of a wood stove, wake up to sunshine streaming through tall windows onto honey-colored pine flooring, and watch from your deck as sunlight fills the river valley and plays across the ridge opposite.

4.91 out of 5 average rating, 285 reviews

Guest favourite

A spacious farm landscape is captured under a clear blue sky, featuring a rustic log home alongside a traditional barn. Surrounding hills are adorned with vibrant autumn foliage, creating a serene setting with open fields and gentle pastures.

Farm stay in Brattleboro

Modern Vermont Farm Stay

Bright and spacious, newly renovated suit, with a full kitchen, cozy gas burning fire place, beautiful views and pastures to explore, and a chance to hang out with the animals in the barn. Just minutes from Brattleboro's down town and amenities.

4.92 out of 5 average rating, 109 reviews