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Vacation rentals in Dummerston

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Top-rated vacation rentals in Dummerston

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

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Guest favorite
A bright living space is surrounded by floor-to-ceiling windows, offering views of vibrant foliage and serene waterways. A small wooden table is positioned on a natural wood floor, highlighting the connection to the outdoor landscape. Warm sunlight filters through the trees, creating a calm ambiance.
Home in Guilford
4.95 out of 5 average rating, 151 reviews

Vermont Mirror House

Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

LocationValueCondition

Guest favorite
Tiny home in Chester
4.98 out of 5 average rating, 130 reviews

Tiny A-Frame Rest House in Woods near Mountains

Newly built A-Frame getaway cabin built in the middle of the woods of Vermont. Unplug from it all at this special space surrounded by nature. Enjoy doing yoga and relaxing on the deck, remote working with fiber optic wifi, utilizing the fire pit to roast smores, or taking a walk around the walking paths on the property! There are also nearby hikes, swimming spots, skiing destinations, and drinking/eating spots! We are 35-40 minutes from Stratton, Mount Snow, Bromley, Okemo, and Magic Mountain!

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Top guest favorite
Tiny home in Wilmington
4.99 out of 5 average rating, 395 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!

LocationFamilyGrill

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, 68 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.

ValueLocationSkiing

Top guest favorite
The treehouse stands elevated among tall trees, featuring a warm wooden exterior and large windows that allow natural light to fill the interior. A deck extends from the structure, leading to a fire pit area surrounded by gravel.
Treehouse in Putney
4.98 out of 5 average rating, 188 reviews

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.

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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, 195 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 .

FamilyLocationSkiing

Top guest favorite
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
4.99 out of 5 average rating, 293 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”.

ValueLocationShared spaces

Top guest favorite
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.
Apartment in Dummerston
4.93 out of 5 average rating, 439 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.

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Top guest favorite
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
4.97 out of 5 average rating, 157 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.

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Top guest favorite
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
4.98 out of 5 average rating, 175 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

LocationValueSolo travel

Top guest favorite
A living area features warm wooden walls and large windows draped with sheer curtains, allowing natural light to fill the space. A comfortable sofa sits adjacent to a television, with a vintage chest and decorative items adding character. A patterned area rug enhances the cozy ambiance.
Apartment in Newfane
4.87 out of 5 average rating, 175 reviews

Apartment at Five Ferns

A cozy spot perfect for quick romantic getaways and an equally comfortable base for longer adventures. Views out your windows show perennial flower gardens and trees. Queen mattress in a spacious bedroom, en-suite bathroom (shower), and a living/dining area with an equipped kitchen are all at your service. Enjoy our yard and trails along the river. We are an easy 5 minute drive to a fantastic restaurant and many more within 15 minutes of driving.

ValueLocationHospitality

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, 317 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.

LocationFamilyView

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
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

LocationValueCondition

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, 47 reviews

Cottage amongst the trees

ValueLocationAccess

Guest favorite
Home in Dummerston
4.94 out of 5 average rating, 33 reviews

Barnside Cottage at Fruition Farm

LocationFamilyPets

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
4.81 out of 5 average rating, 77 reviews

Coverd Bridge Cabin

LocationValueLaundry

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

ValueFamilyAccess

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

Diana's TreeTop Retreat - skiing & hiking

LocationFamilyComfort

Superhost
Home in Putney
4.73 out of 5 average rating, 41 reviews

Mountain Top Escape

FamilyLocationDecor

Top guest favorite
Cabin in Townshend
5.0 out of 5 average rating, 83 reviews

Goldfinch Hollow: Tucked Within 5 Private Acres

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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