Become a host

Vacation rentals in Dummerston

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Dummerston

Guests agree: these stays are highly rated for location, cleanliness, and more.

1 of 1 pages1 / 1
Top guest favorite
A compact red tiny house is positioned among tall trees, with sunlight shining on its deck. Snow blankets the ground, providing a serene winter backdrop. The house features large windows that invite natural light and a wooden deck accessible by steps.
Guesthouse in Dummerston
5.0 out of 5 average rating, 48 reviews

Cottage amongst the trees

Relax in this calm & stylish space. Fully renovated in December 2024, this tiny house sits on 14 acres of land overlooking a seasonal pond, gardens & patios. Hosts live in the main house built in 1803. Great for the travelling professional who is looking for a peaceful & comfortable place to unwind after a long shift at the hospital or day on the slopes. Minutes to downtown Brattleboro yet in a rural setting. Equidistant to exits 3 or 4 on I-91; close to Putney, Bellows Falls, Keene & Mt. Snow.

LocationValueHospitality

Top guest favorite
Home in Dummerston
4.95 out of 5 average rating, 37 reviews

Barnside Cottage at Fruition Farm

Welcome to the Barnside Cottage at Fruition Farm, a newly renovated retreat on 182 acres in southern Vermont. Just 24 minutes from Mount Snow, it offers comfort, privacy, river access, a full-length deck, and four-season beauty. Enjoy hiking, foliage, gardens, and peaceful views. Camp at your own private riverside campsite, complete with fire pit and picnic area. Owners are nearby for support, and up to two dogs are welcome. A cozy, stylish getaway designed for rest, connection, and adventure.

LocationFamilyQuiet

Guest favorite
A comfortable white sofa with decorative pillows is positioned against a light wall. A small, light-colored side table holds a potted plant. Natural light streams in through a nearby window, illuminating the wooden floor and a blue woven rug beneath.
Apartment in Dummerston
4.94 out of 5 average rating, 270 reviews

HeART Barn Retreat

Peaceful, romantic retreat in this stunningly large and magical barn. This 1850's historic remodeled barn apartment 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.

FamilyValueSleep quality

Top guest favorite
A metal sign displaying the name 'River Shack' is mounted on a wooden exterior. The wood paneling features a natural finish, while silhouettes of trees are incorporated into the design, emphasizing the cabin's rustic charm.
Cabin in Dummerston
4.97 out of 5 average rating, 69 reviews

Cozy Riverfront Cabin-Ski, Swim, Fish, Float, Hike

The River Shack is a quintessential cozy cabin in the quiet woods of Southern Vermont. Right next to the Historic Dummerston Covered Bridge. Surrounded by nature, Find yourself relaxing to the calming sounds of the West River just steps away from the back porch. The Shack features A small sandy beach and 100 feet of sparkling river view. Perfect for a dip, snorkel, cast, or a lazy tube ride down river. You’ll find endless activities including hiking, waterfalls, swim, golf, fishing, ski.

FamilyValueCondition

Top guest favorite
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.
Apartment in Brattleboro
4.99 out of 5 average rating, 200 reviews

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 .

LocationValueRiver

Guest favorite
A charming house is nestled among greenery, featuring a screened-in porch with a red door. Low shrubs and flowering trees frame the entrance. Soft light filters through the trees, highlighting the natural surroundings and offering a sense of tranquility.
Home in Dummerston
4.89 out of 5 average rating, 45 reviews

Woodsy Retreat Near Skiing, Private Pool in Summer

Relax in delightful 2-bedroom house in Dummerston. Located at end of a gravel road, private parking. Peace and quiet, yet Downtown Brattleboro only 10 minutes down road. Cozy and spacious living room, full kitchen and dining area. Private swimming pool and deck, private yard and 3-acre woods. Beautiful views up Knapp Road at Elysian Hills Farm. Hiking, kayaking, skiing -- Mt. Snow only 35 minutes away. Lots to do in surrounding area -- come see the charm of Southern Vermont!

FamilyLocationComfort

Superhost
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
4.98 out of 5 average rating, 160 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.

LocationValueSleep quality

Guest favorite
Home in Dummerston
4.96 out of 5 average rating, 133 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.

LocationFamilyWalkability

Top guest favorite
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
4.99 out of 5 average rating, 318 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.

FamilyLocationAccuracy

Top guest favorite
Apartment in Brattleboro
4.99 out of 5 average rating, 117 reviews

Guest House @ 120

Unforgettable designer stay in the heart of downtown Brattleboro. Curated art, luxe finishes, and boutique comfort set this experience apart. Walk to the best cafes, boutiques, and galleries. Enjoy a chef’s kitchen, plush bed, quaint bath, and fast Wi-Fi. Every detail is elevated, every corner styled. Steps from Amtrak, wrapped in Vermont charm. Perfect for escapes, retreats, or inspired work. You won’t want to leave.

LocationValueDecor

Guest favorite
Cabin in Dummerston
5.0 out of 5 average rating, 12 reviews

Diana's TreeTop Retreat - skiing & hiking

High among maples and pines, this light-filled hideaway offers a front-row seat to Vermont’s changing seasons. Minutes from Brattleboro, paddle the West River, ski nearby slopes, or stroll to the covered bridge. Inside, the warmth of longtime steward Diana - poet, farmer, artist - lingers in every beam and sunlit corner. Come to rest, write, cook, or simply watch the light shift and feel the rhythm of Vermont.

LocationFamilyLayout

Top guest favorite
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
4.95 out of 5 average rating, 376 reviews

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!

FamilyLocationHiking

Popular amenities for Dummerston vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Dummerston's top sights

Putney Mountain Winery and Spirits

21 locals recommend

Black Mountain

16 locals recommend

Green Mountain Spinnery

8 locals recommend

Other great vacation rentals in Dummerston

Guest favorite
The exterior of a charming red church stands against a bright blue sky, complemented by scenic mountain views. A vibrant tree with red foliage is visible in the foreground, along with a grill placed outside by the entrance. The building features distinctive architectural elements, including a tall steeple.
Place to stay in Dummerston
4.84 out of 5 average rating, 87 reviews

The Church Sanctuary

FamilyValueLayout

Top guest favorite
Chalet in Brookline
4.97 out of 5 average rating, 79 reviews

Cozy Vermont Chalet

LocationValueQuiet

Superhost
A semi A-frame structure is surrounded by lush greenery. The exterior features dark wood siding and large windows, allowing natural light to enter. A wooden deck with steps provides access to the front door, inviting guests into the peaceful retreat.
Home in Dummerston
4.76 out of 5 average rating, 79 reviews

Coverd Bridge Cabin

ValueLocationIndoor spaces

Guest favorite
Two vintage cottages are displayed, each featuring a green metal roof and white exterior. A propane grill is positioned in the foreground, alongside a fire pit and picnic table. Lush green grass surrounds the cottages, providing a natural outdoor setting.
Cabin in Dummerston
5.0 out of 5 average rating, 12 reviews

Vintage Cottage 3 at Brattleboro KOA

LocationValueAccuracy

Guest favorite
A spacious wooden deck is surrounded by lush greenery and colorful flower pots. A round table with four chairs is positioned under a large turquoise umbrella. Two lounge chairs are also present, along with a grill nearby, creating an inviting space for outdoor relaxation.
Home in Putney
4.77 out of 5 average rating, 60 reviews

Year Round Mountain Retreat

LocationFamilyHospitality

Guest favorite
Home in Putney
4.94 out of 5 average rating, 18 reviews

Charming Putney Village Home!

FamilyLocationComfort

Top guest favorite
Home in Newfane
5.0 out of 5 average rating, 47 reviews

Pondside Retreat in Southern Vermont

ValueLocationSkiing

Top guest favorite
A charming Cape-style house with a light-colored exterior is showcased amidst a lush green landscape. A red barn is positioned in the background, surrounded by trees under a clear blue sky. The ample yard offers a serene rural setting.
Home in West Brattleboro
4.93 out of 5 average rating, 88 reviews

Private Brookside Farmhouse

ValueLocationNearby

Frequently Asked Questions

  • What are the best places to stay in Dummerston?

    Dummerston has vacation rentals in rural neighborhoods, near natural parks, and close to art studios. Many homes offer quiet surroundings, easy access to hiking trails, and family friendly amenities. Local hosts emphasize warm hospitality and a connection to the area’s tradition.

  • What are the best things to do in Dummerston with kids?

    Kids often enjoy visits to covered bridges, nature walks in local parks, and picking produce at farm stands. Opportunities for outdoor play, seasonal workshops, and exploring art studios contribute to family activities. The area emphasizes hands-on, outdoor experiences.

  • What are some of the best things to do in Dummerston?

    Explore hiking trails, visit historic covered bridges, and discover local art galleries and farm stands. Nature and history are often highlighted, with rural landscapes inviting outdoor activities. Seasonal festivals and markets contribute to the community’s atmosphere.

  • How is the weather in Dummerston?

    Dummerston has cold winters, with temperatures around 13–32°F (-11–0°C), and mild summers near 57–81°F (14–27°C). Spring and fall bring fresh air and colorful scenery, though rainfall is quite frequent throughout the year. Packing layers and a waterproof jacket is helpful.

  • When is the best time to visit Dummerston?

    Many visitors appreciate Dummerston in autumn for its vibrant foliage and rural harvest celebrations, while late spring and summer bring mild temperatures and outdoor festivals. Winter attracts those interested in snowy landscapes and cozy indoor activities. Each season highlights different aspects of the area’s traditions.

  • What are the best places to visit in Dummerston?

    Historic covered bridges, the town’s rural parks, and local art galleries are popular places to explore. Visitors often enjoy farm stands featuring Vermont products and community spaces tied to the area's history. Natural landscapes create appealing spots for relaxation.

  • What are some hiking trails in Dummerston?

    Dummerston has woodland paths, riverside routes, and scenic hill trails for various skill levels. Forests and open fields create rewarding hikes, especially in autumn when leaves are vibrant. Local parks and natural reserves are often suggested for a quiet outdoor experience.

  • What are some family activities we can do in Dummerston?

    Families often enjoy nature walks, picnics in local parks, and visits to farm stands for seasonal produce. Local art studios may have workshops, and exploring covered bridges is a favorite. Activities are grounded in the area’s outdoor scenery and community spirit.

  • What are some of the best day trip ideas from Dummerston?

    Day trips from Dummerston frequently include exploring nearby small towns with art communities, visiting riverside parks, and touring maple syrup operations. Regional nature reserves or local history museums give insight into Vermont’s broader culture. Seasonal festivals in neighboring areas are often suggested.

  • Are there any pet friendly accommodations available in Dummerston?

    Dummerston has pet friendly vacation rentals, especially in rural neighborhoods around forested areas and local farms. Many hosts welcome pets with prior notice, and nearby walking paths make outings easy. Review listing details to confirm pet policies.

  • What are some local tips for visiting Dummerston?

    Dummerston has scenic rural landscapes, so comfortable shoes and a camera are often recommended. Locals appreciate slower-paced explorations and suggest checking for seasonal activities, especially in autumn when the foliage changes. Many locally owned shops and farm stands enhance the area’s experience.

  • What is Dummerston known for?

    Dummerston is known for its historic covered bridges, rural landscapes, and vibrant autumn foliage. Locally rooted traditions such as small-scale farming and community arts add to its distinct atmosphere. Outdoor activities and seasonal produce are frequently highlighted.

  • What are the best hidden gems to explore in Dummerston?

    Dummerston’s historic covered bridges, small antique shops, and rural art studios are frequently suggested as hidden gems. Quiet river spots and farm stands also provide unique local experiences. Exploring off the main roads reveals much of the area’s charm.

  • What are the best foods to try in Dummerston?

    Locally made maple syrup, fresh dairy products, and homemade baked goods are frequently suggested flavors in Dummerston. Farm stands often feature vegetables, artisanal cheeses, and preserves rooted in Vermont culinary traditions. Seasonal pies and cider add to the experience.

  • What should I bring for a trip to Dummerston?

    Pack layered clothing, sturdy walking shoes, and a waterproof jacket due to changing weather and frequent rain. A camera, snacks, and reusable water bottles are also welcomed for outdoor excursions. If planning to hike or picnic, consider bringing insect repellent.

  • What is the nightlife in Dummerston like?

    Dummerston has a quiet nightlife, centered on local cafés, occasional live music, and small social gatherings in community spaces. Nearby towns may have additional venues and events. Evenings often focus on relaxed settings and neighborly interactions.

  • What are the most popular events or festivals in Dummerston?

    Dummerston has autumn festivals like the Apple Pie Festival and Heirloom Apple Day, which celebrate local produce and community traditions, especially during peak foliage in October. Seasonal art gatherings and harvest celebrations are also frequently suggested, bringing together local makers and neighbors.

  • Are there family friendly vacation rentals in Dummerston?

    Family friendly vacation rentals can be found in Dummerston’s rural neighborhoods and near open park spaces. Many homes have ample room for outdoor play and gathering, with easy access to local nature spots. Hosts often highlight amenities suitable for families.

Destinations to explore