Holiday rentals 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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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

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!

FamilyLocationDecor

4.95 out of 5 average rating, 160 reviews
Top guest favourite
Treehouse in Wilmington

Beautiful timber-frame treehouse

The timber frame treehouse is a perfect couples retreat. The home is custom built with hardwood maple trees cut down and milled right on the property. The deck has a barrel sauna, cold or hot cedar soaking tub, a propane fire pit, a wood burning chiminea fire pit, and a bar top for outdoor dinning. The inside has a stone fireplace, fully equipped kitchen, tile shower, projector with dvds, books, board games, chandelier, and dimmable lighting for any mood. This home is truly one of a kind.

FamilyLocationNearby

5.0 out of 5 average rating, 123 reviews
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.
Flat in Brattleboro

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 .

FamilyValueAmenities

4.99 out of 5 average rating, 205 reviews
Guest favourite
Flat in Dummerston

1850’s 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.

LocationValueNearby

4.91 out of 5 average rating, 515 reviews
Top guest favourite
A gently sloping lawn leads up to the light-colored building, framed by lush gardens and vibrant greenery. A pair of purple Adirondack chairs sits invitingly on the grass, offering a serene spot to enjoy the surrounding landscape.
Flat in Marlboro

Shakespeare’s Folly Side Farm and AirBnB.

Located on a gorgeous south-facing hillside in Marlboro, VT, Shakespeare's Folly Side Farm is a light, airy, quiet apartment with stunning views, beautiful gardens, and walking paths. We have friendly a dog, vegetable and flower gardens and a small orchard, with raspberries and blueberries. Free picking in the summer. A magical and inspiring place of rolling lawns and 40 mile views yet so close to the many rich cultural and recreational options in southeast Vermont.

FamilyValueGrill

4.93 out of 5 average rating, 311 reviews
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

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.

FamilyLocationRiver

4.98 out of 5 average rating, 161 reviews
Guest favourite
Home in Dummerston

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.

ValueLocationKitchen

4.96 out of 5 average rating, 133 reviews
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

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.

ValueFamilySleep quality

4.99 out of 5 average rating, 320 reviews
Top guest favourite
A modern home is situated on a sloped driveway surrounded by trees, with a green lawn and landscaped stone features. Solar panels are visible on the roof. Two vehicles are parked under a covered deck, which extends from the main structure.
Flat in Brattleboro

Contemporary forest eco-retreat, mountain views

This is an open, one-Bdm apartment on the lower level of our hillside home, surrounded by gardens and forests with stunning views. Your space is 719 sf + access to laundry. We welcome all kinds of people, regardless of race, ethnicity, gender, etc. We may ask questions before accepting people who don’t have many prior reviews. We don't take pets, sorry.

ValueLocationAmenities

4.95 out of 5 average rating, 220 reviews
Top guest favourite
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

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!

ValueLocationBack garden

4.95 out of 5 average rating, 377 reviews
Top guest favourite
A charming wooden house is surrounded by a snowy landscape, showcasing a large deck and steps leading to the entrance. Snow-covered trees and a clear blue sky enhance the serene setting. The structure features multiple levels, presenting a cozy, inviting exterior.
Cottage in Newfane

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.

FamilyLocationHeating

4.91 out of 5 average rating, 285 reviews
Guest favourite
A spacious farm landscape is captured under a clear blue sky, featuring a rustic log home alongside a traditional barn. Surrounding hills are adorned with vibrant autumn foliage, creating a serene setting with open fields and gentle pastures.
Farm stay in Brattleboro

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.

LocationValueOutdoor spaces

4.92 out of 5 average rating, 109 reviews

Popular amenities for Dummerston holiday rentals

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.