Holiday houses in Dummerston

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Top-rated holiday rentals in Dummerston

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

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Top Guest favourite
A cozy tiny cabin, constructed with wooden beams and a sloped roof, is situated among tall trees. The porch features a railing, inviting seating, and a lantern. Sunlight filters through the foliage, casting a soft glow on the forest floor covered in pine needles.
Treehouse in Brookline
4.98 out of 5 average rating, 269 reviews

Glamping Cabin with Hot Tub on Flower Farm

<b>Vermont's Most Wish Listed</b> ﹏﹏﹏ Nestled in a wooded grove on Tanglebloom Flower Farm, this unforgettable glamping-inspired farm stay invites you to escape the everyday & immerse yourself in nature - comfortably. Designed with a clear roof looking up to the trees and screened sides to let in the breeze, the handmade tiny cabin invites you to slow down. Explore southern Vermont's hikes, farmer's markets & swimming holes or stay put. Perfect for a romantic couples retreat or solo getaway.

Guest favourite
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, 146 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!

Top Guest favourite
Tiny home in Wilmington
4.99 out of 5 average rating, 391 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!

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.
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 .

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
4.99 out of 5 average rating, 292 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”.

Top 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.
Apartment in Dummerston
4.93 out of 5 average rating, 436 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.

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
4.97 out of 5 average rating, 156 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.

Top Guest favourite
The garden features raised vegetable beds surrounded by a wooden fence. In the background, the charming former church building with a pointed steeple is visible, framed by vibrant autumn foliage in shades of red and orange.
Guest suite in Brattleboro
4.95 out of 5 average rating, 635 reviews

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.

Guest favourite
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, 173 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.

Guest favourite
Home in Dummerston
4.96 out of 5 average rating, 132 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.

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
4.99 out of 5 average rating, 316 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.

Top 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
4.96 out of 5 average rating, 202 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.

Popular amenities for Dummerston holiday rentals

When is the best time to visit Dummerston?

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Avg. price$302 NZD$302 NZD$219 NZD$188 NZD$224 NZD$219 NZD$293 NZD$254 NZD$241 NZD$254 NZD$228 NZD$233 NZD
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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.

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