Waterfront vacation rentals in Plymouth

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Top-rated waterfront rentals in Plymouth

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Guest favorite

A serene scene features a spacious house nestled beside a tranquil pond. Vibrant autumn foliage enhances the landscape, with a mix of orange, yellow, and green trees lining the property. The grassy area invites exploration, while reflections on the water add to the peaceful ambiance.

Home in Grafton

4.94 out of 5 average rating, 126 reviews

The Grafton Chateau

Welcome to the Grafton Chateau, a gorgeous secluded and private country retreat for all of your family and friends. With six bedrooms and a den, four baths, two fireplaces, a sauna and a large private pond beautifully situated on 67 acres of woodlands, the Grafton Chateau is the perfect comfortable home base for ski trips, hiking, antiquing, or just enjoying the scenery while you sit around the fire pit. The garage has outdoor recreation gear, like snowshoes and sleds. The den has a variety of toys, and games for kids and adults. The whole house, sauna house, barn and all 67 acres are all yours! We are always available by phone, text, or email if you have any questions. Grafton is just about the most charming Vermont town you can find and is convenient to four ski mountains and every other outdoor activity you can imagine.

Top guest favorite

A cozy living area showcases a comfortable sofa adorned with patterned cushions and a soft throw. A rustic coffee table sits in front, complemented by stylish armchairs. Natural light filters through large windows, illuminating the modern kitchen with dark cabinetry in the background.

Tiny home in Fairlee

5 out of 5 average rating, 147 reviews

Private, 1 bedroom boutique tiny home

This boutique tiny home is situated in the picturesque Upper Valley of Vermont. The nearly 50 acres of private land is equal parts woods and water. You will wake to the mooing of dairy cows. Have your coffee on the porch while watching birds dive for their breakfast on the pond. Inside you will find every modern amenity. A fully appointed chef's kitchen. A living area filled with comfy furnishings and a cozy fireplace. Upstairs is a queen bedroom with an ensuite double showered bathroom. Heaven!

Top guest favorite

The cabin is illuminated at dusk, showcasing a rustic exterior with a distinctive cupola. Glass French doors provide a view into the warmly lit interior. A wooden pathway leads to the entrance, bordered by a landscaped yard with trees and decorative elements.

Farm stay in Croydon

4.98 out of 5 average rating, 164 reviews

Lighthouse Inn the Woods~peaceful farmhouse stay

Our cabin is perfectly private, comfortably cozy, and surprisingly sunny. Fully stocked kitchen allows for easy meal prep away from home. Comfy seats for everyone around the TV or table. You'll feel so at home you might never want to leave. A good night's sleep is paramount in a peaceful vacation. We offer only 100% cotton or linen bed linens on our extraordinarily comfortable beds as well as black out curtains in each bedroom. Book your stay to let us show you what luxury and rest feel like.

Top guest favorite

A modern chalet is situated among lush greenery, featuring a sloped roof and large windows. A cozy outdoor seating area surrounds a fire pit on a grassy lawn, inviting relaxation in a natural setting. A storage area for firewood is visible beside the structure.

Chalet in Woodstock

4.98 out of 5 average rating, 108 reviews

Falcon House: VT Chalet w/Sauna, Bike to Village

Welcome to Falcon House! A modern VT chalet w/sauna at the edge of a 60 acre forest ∙ Outdoor Finnish sauna, shower, yoga platform & hiking trails ∙ 5 min to Woodstock village, 20 min to ski Killington ∙ Spotlessly clean, tastefully furnished, well stocked with thoughtful amenities ∙2 bedrooms, 2 full baths. Lofted king master has ensuite +Lower level den w/double futon ∙ Chefs kitchen, fireplace, 2 TVs & WiFi ∙ Brookside deck w/BBQ & dining ∙Follow Falcon House on Social @falcon_house_vt

Top guest favorite

The image captures a serene lakeside property surrounded by trees. Two private decks are visible alongside the water, with steps leading to the docks. Canoes and kayaks are neatly arranged, enhancing the outdoor experience. The warm glow from the home suggests a welcoming environment.

Home in Poultney

4.94 out of 5 average rating, 339 reviews

Waterfront Vermont Lake House w/ Canoe/Kayak/SUPs

We invite you to come stay and experience all of the beauty that Vermont has to offer at Lake St. Catherine. Located on the west side of the lake off a quiet private drive with almost 100ft of lake frontage, there are few spots with a better view. Watch the sun rise each morning from either our private decks. Explore the lake by canoe or kayak; both available for our guests. If the dates you're looking for are booked, message us for availability at our second location! Follow us @vtlakehouse

Guest favorite

A captivating sunset paints the sky with hues of orange, pink, and purple, with rolling hills silhouetted in the foreground. The distant mountains create a serene backdrop, accentuating the natural beauty of the secluded setting.

Home in Plymouth

4.95 out of 5 average rating, 252 reviews

Top of the World! Jacuzzi! Private Hiking Trails!

Welcome to one of the most unique "retreats" in Vermont! Perched atop a private mountain with beautiful 100 mile views! Ideally located between Killington (7 miles) & Okemo resorts, near Woodstock. Relax in the Jacuzzi while enjoying the views and stars. Private, peaceful hiking trails and waterfalls, with trail maps. Direct access to the Green Mtn. Forest. NEW-There's a picnic table near the water falls and Buddha Rocks. Bring lunch & enjoy your own nature paradise! Small private beach!

Guest favorite

The exterior of Bearfoot Cottage is highlighted, featuring a combination of wood and metal finishes. A spacious deck with steps leads to the entrance, framed by large windows. A fire pit sits nearby, complemented by comfortable seating arrangements on the gravel surface.

Tiny home in Chester

4.97 out of 5 average rating, 150 reviews

Bearfoot Cottage: Tiny House w/ Hot Tub near Okemo

Tiny living at its best! Welcome to Bearfoot Cottage, a custom-designed Tiny House escape nestled on 15 acres in Southern Vermont. Enjoy the entire property to yourself with hot tub, Char-Griller BBQ, & Solostove firepit. Hike or snowshoe Ladybug Trail to our babbling brook. Then explore the best of Okemo Valley all at your fingertips! Ski/Snowboarding (+more Winter sports), biking, hiking, fishing, dining, breweries, and live music/nightlife. Your vacation is what you make it!

Guest favorite

A spacious living room features a comfortable sofa and armchair, enhancing relaxation. A large television is positioned in front, with decorative elements and artwork on the walls. Soft lighting from lamps and windows creates a welcoming ambiance in the well-designed space.

Guest suite in Clarendon

4.95 out of 5 average rating, 179 reviews

River House Apartment - Dog friendly

Entire downstairs of a house with one double bed. There is nice bathroom with shower. There is a microwave, coffee, massage chair, outdoor grill and picnic table. Internet and cable provided with fire stick for the TV. Fire pit and hot tub are shared by other guests. Up to three and all size dogs or pets are allowed and welcome. The three acres has a lovely place for them to run and has been sprayed for ticks and mosquitos. Please note: key replacement $30 if lost or taken

Guest favorite

An interior view showcases a modern staircase with wooden steps and a metal railing, leading to a second floor. Natural light floods the space through large glass windows, illuminating the wooden walls and a stone fireplace. A green plant adds a touch of nature.

Home in Londonderry

4.99 out of 5 average rating, 141 reviews

Modern 3-bedroom A-frame in Londonderry w/ Pond

This 1970s A-Frame has been newly renovated and is ready to host guests. This home is located on a 2.6 acre property complete with a swimmable pond , outdoor firepit (snow dependent) and dining al fresco. It's located only a few minutes away from amenities such as Londonderry Market, Pingree Park, Lowell Lake and several restaurants. For skiing, this home is in proximity to Magic (8min), Bromley (9min), Okemo (25 min) and Stratton (20 min).

Top guest favorite

The Kingsley Grist Mill is positioned alongside a flowing river, surrounded by trees showcasing autumn colors. A historic covered bridge is visible in the distance, enhancing the landscape. The building features multiple stories with varying textures and roof styles, reflecting its rich history.

Castle in Clarendon

4.98 out of 5 average rating, 479 reviews

Kingsley Grist Mill, w/ Private Beach & Waterfall

One of the "World's Most Amazing Vacation Rentals " as seen on the exciting NetFlix series, s.2, ep.7 and on HGTV's "You Live in What?, s.2, ep.1. Join us this season for the romance, the history, the breakfast, the natural mineral spring tap water, the concert, the rafting, the architecture and the legacy of the KGM, Vermont's Wright-esque falling water masterpiece. Come make history with us ! Near Killington & Okemo Mtns.

Guest favorite

A tranquil scene captures a log cabin nestled by a pond, surrounded by trees. The clear water reflects the cabin and vibrant foliage, creating a serene atmosphere. Tall grasses frame the pond's edge, while the landscape showcases the lush greenery of Vermont.

Cabin in South Royalton

4.96 out of 5 average rating, 195 reviews

Cozy 4-season Cabin on Pond - "East Cabin"

Take refuge in a cozy log cabin with abundant access to Vermont's Green Mountains and rolling foothills. A quick drive to Woodstock and Quechee, the cabin is located on quiet dirt road with beautiful south-facing views overlooking the town of South Royalton, just a mile away. Spring-fed pond is steps from the cabin, take a dip! Follow the trails through the woods and fields and enjoy this pristine piece of Vermont.

Guest favorite

A spacious living area features large floor-to-ceiling windows offering a view of the green outdoor space. A plush sofa, accented with colorful cushions, sits in front of a wooden coffee table. A modern dining area is visible in the background, illuminated by soft lighting.

Home in Winhall

4.98 out of 5 average rating, 393 reviews

Stunning mid-century house on 2.5 private acres

Stay at our relaxing, mid-century retreat! The house was built in the 60s but has modern amenities. A 4-wheel-drive vehicle is recommended. Our house is conveniently located 7 miles from Stratton and 12 miles from the outlets/restaurants in Manchester. Floor to ceiling windows provide a stunning view of the property. Please note, the house has a non-working fireplace.