
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.

Treehouse Haven in Putney-All Seasons
Peaceful, private & fully equipped four-season treehouse, surrounded by nature. ☽ Private & secluded ☽ Central to activities & necessities ☽ Firepit, pellet stove, deck, grill & fully stocked kitchen ☽ Scrupulously clean, unscented products ☽ Clean composting outhouse ☽ Tea & local coffee ☽ Hot outdoor shower-Closed Nov-April ☽ 45min to ski resorts ☽ Swimming holes & hikes ☽ WiFi & electricity Retreat from the business of life; romance, with the family, or even a remote work sanctuary.
4.97 out of 5 average rating, 197 reviews
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
~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
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
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
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
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
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
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
House on a hill
Keep it simple at this peaceful and centrally-located large studio home. Enjoy your coffee while sitting on the screened in porch with beautiful local views. Just 3 miles to Brattleboro, VT and 12 miles to Keene, NH you can spend the day hiking in VT and the night in downtown Keene.
4.98 out of 5 average rating, 114 reviews
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
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 reviewsPopular amenities for Dummerston family-friendly rentals
Family-friendly home rentals with a hot tub

Beautiful Timber Frame Retreat
5.0 out of 5 average rating, 403 reviews
Vermont Mirror House
4.95 out of 5 average rating, 156 reviews
Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba
4.95 out of 5 average rating, 267 reviews
Secluded Farmhouse Retreat - stunning views
4.94 out of 5 average rating, 198 reviews
The House of Pi
4.88 out of 5 average rating, 121 reviews
Private Apt. on Farm, Hot Tub with views!
4.93 out of 5 average rating, 281 reviews
Mt Snow Chalet: Peaceful Escape w/Hot Tub
5.0 out of 5 average rating, 131 reviews
HYGGE HOUSE Luxe HotTub, Sauna, Fall Leaves, Ski
4.96 out of 5 average rating, 174 reviewsFamily- and pet-friendly home rentals

Clark Farm-2 Master-Suites, Great kitchen, views!
4.95 out of 5 average rating, 115 reviews
Peaceful Beautiful Mountain Home Spectacular Views
4.91 out of 5 average rating, 116 reviews
Apple Blossom Cottage: A Tiny House
4.94 out of 5 average rating, 1379 reviews
The Chal-A-Frame Vermont
4.99 out of 5 average rating, 220 reviews
Snug Chalet - Wi-Fi + Close to Mount Snow
4.97 out of 5 average rating, 146 reviews
Carriage Barn - Marlboro
4.89 out of 5 average rating, 682 reviews
Shakespeare’s Folly Side Farm and AirBnB.
4.93 out of 5 average rating, 309 reviews
Cozy Cabin in Southern VT
4.95 out of 5 average rating, 236 reviewsFamily-friendly home rentals with a pool

Silver Brook Cabin
4.95 out of 5 average rating, 180 reviews
The Brick House on Washington Street
4.93 out of 5 average rating, 249 reviews
Family-friendly 4BR | Pools Hot Tub | Near Mt Snow
4.89 out of 5 average rating, 180 reviews
Leonard’s Log - Private Hot Tub, Fire Pit, A/C
4.92 out of 5 average rating, 223 reviews
Modern Cottage between Stratton and Mount Snow VT
4.97 out of 5 average rating, 113 reviews
The 1770 House
4.9 out of 5 average rating, 143 reviews
Rocky Ledge: Cozy Pet-Friendly 3BR Log Cabin
4.92 out of 5 average rating, 161 reviews
Log Cabin w/ Hot Tub & Fire Pit - Stratton/Mt Snow
4.9 out of 5 average rating, 250 reviewsDestinations to explore
- New York Holiday rentals
- Montreal Holiday rentals
- Philadelphia Holiday rentals
- Boston Holiday rentals
- Quebec City Holiday rentals
- Jersey City Holiday rentals
- Portland Holiday rentals
- Newark Holiday rentals
- Mont-Tremblant Holiday rentals
- Atlantic City Holiday rentals
- Newport Holiday rentals
- Providence Holiday rentals
- Okemo Mountain Resort
- Stratton Mountain
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Jiminy Peak Mountain Resort
- Monadnock State Park
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Bousquet Mountain Ski Area
- Hildene, The Lincoln Family Home
- Killington Resort
- Mount Monadnock
- Bromley Mountain Ski Resort
- Emerald Lake State Park
- University of Massachusetts Amherst
- Massachusetts Museum of Contemporary Art
- Mount Sunapee Resort
- Mount Greylock
- Mount Holyoke College
- Camp Plymouth State Park
- The Montague Bookmill
- Jamaica State Park
- Bridge of Flowers
- Magic Wings Butterfly Conservatory and Gardens





