
Family-friendly vacation rentals in Dummerston
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Top-rated family-friendly rentals in Dummerston
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Clark Farm-2 Master-Suites, Great kitchen, views!
The historic Clark Farm boasts beautiful mountain views as well as of our apple orchard and early 19th Century barn. The farmhouse sleeps 8 comfortably with 2 king-size master suites that are tucked away each on their own floor. The queen room and the kids room (twins) share 1.5 baths in the "new" side of the house. The spacious light-filled farmhouse has an open floor plan with a gas fireplace in both the living room and tv/game room. Outdoors enjoy the 8 adirondack chairs and a fire pit .
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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 .
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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”.
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~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.
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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.
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Charming studio in renovated 19th century church.
This spacious studio apartment is located in the former Swedish Congregational Church in historic Swedeville, a secluded hilly neighborhood built by Swedish immigrants in the 1800's. For years it housed Rick and Liza’s stained glass studio, which they have now lovingly and creatively transformed into a residence. The rental is minutes from the interstate and one mile from downtown Brattleboro, but the neighborhood has a rural and somewhat European flavor to it.
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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.
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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.
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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.
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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.
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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.
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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.
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Popular amenities for Dummerston family-friendly rentals
Family-friendly home rentals with a hot tub

Vermont Mirror House
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Beautiful timber-frame treehouse
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Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba
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The House of Pi
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Modern Downtown Escape HotTub Fire Pit Games 12ppl
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Private Apt. on Farm, Hot Tub with views!
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Mt Snow Chalet: Peaceful Escape w/Hot Tub
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Mountain View Retreat: 5 Mi to MT Snow, Hot Tub
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Family- and pet-friendly home rentals

Beautiful rustic woods and fields retreat.
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The Chal-A-Frame Vermont
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Apple Blossom Cottage: A Tiny House
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Cozy Cabin in Southern VT
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Shakespeare’s Folly Side Farm and AirBnB.
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Adorable home in Newfane
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Peaceful Beautiful Mountain Home Spectacular Views
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Snug Chalet - Wi-Fi + Close to Mount Snow
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Family-friendly home rentals with a pool

Silver Brook Cabin
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Modern Cottage between Stratton and Mount Snow VT
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Cozy 4BR Cabin | Pools & Hot Tub | Near Mt Snow
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The 1770 House
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The Brick House on Washington Street
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Mid-mod VT Dream Chalet near skiing, lake & forest
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Walk to Mt. Snow-Spa-Summer Pool
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Leonard’s Log - Private Hot Tub, Fire Pit, A/C
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Destinations to explore
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- 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
- Bromley Mountain Ski Resort
- Mount Monadnock
- 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





