Waterfront vacation rentals in Madison County

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Top-rated waterfront rentals in Madison County

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Top guest favorite
A scenic view of a pond surrounded by open land and trees reveals a family enjoying the outdoors. Mountains are visible in the background, creating a peaceful and spacious setting. The landscape includes a small structure near the pond, contributing to the rural charm.
Home in Hood
4.98 out of 5 average rating, 310 reviews

Firnew Cottage

A perfect family getaway from the city in the heart of Virginia Wine Country, 15 min from Shenandoah National Park, 30 min from Charlottesville. Private cottage on 265 acres with 3 mi. hiking trail, overlooks 2 ponds/playhouse offers complete farm experience. Walk to swimming hole on river, canoe/fish in lake, feed peacocks/ goats, collect fresh eggs. Great sunsets. Fire-pit. Close to wineries, breweries, Montpelier, Monticello - only 1.5 hrs to DC/Richmond. Pet friendly. Tour included.

Guest favorite
A living area features a dark leather armchair and a black sofa adorned with decorative pillows. A round coffee table sits on a patterned rug, while a floor lamp provides soft lighting. Large windows offer a view of the surrounding nature.
Cottage in Hood
4.95 out of 5 average rating, 117 reviews

The Cozy Conway Cottage

Enjoy peace and quiet along the Conway River. This relaxing getaway is about 1/4 mile off of rte 230. The cottage was an original one-room cabin with a centrally located wood stove/fireplace. It now boasts 2 bedrooms, 1 bathroom, a full kitchen, large windows and a patio/deck with river views. During the fall and winter months, you can see the sunset over the mountains of the National park. It’s a 20 min drive to the Shenandoah National Park entrance and 5 minutes from Early Mountain Vineyard.

Top guest favorite
A luxury tiny cottage is showcased amidst a lush green landscape, with a curved outdoor sauna adjacent to the home. The gravel pathway leads to a spacious deck with steps, while expansive views of rolling hills and trees form the backdrop, complementing the serene setting.
Tiny home in Madison
5 out of 5 average rating, 150 reviews

Luxury Tiny Home 2: Sauna, Farm & Mountain Views

The retreat at Rooted Land Co. consists of 1 farmhouse and 3 luxury tiny cottages on 350 private acres nestled at the base of the Blue Ridge Mountains with more than 1-mile of Rapidan River frontage. Each home is spaced with privacy in mind and positioned with breathtaking views. Countless outdoor activities including fishing, hiking, and wildlife viewing provide a unique experience during your stay. Rooted Land Co. is located just minutes from wineries, breweries, and Shenandoah National Park.

Superhost
A charming cottage is set against a backdrop of lush trees. A welcoming front porch with white railings encircles the entrance. The property features landscaped areas with low shrubs and concrete steps leading to the front door.
Home in Stanardsville
4.89 out of 5 average rating, 222 reviews

The Conway House

Get away on the Conway, a place to recharge, relax and explore. Located just outside a back entrance to the Shenandoah national park. Walk, run, or bike these lightly traveled country roads to access the trail heads. This private cottage is the ideal location for visiting the Shenandoah national park, hiking, fishing, biking, wineries, and getting away to relax. This newly remodeled mountain retreat is updated with modern decor and all the essentials for an unforgettable mountain getaway.

Top guest favorite
Cabin in Madison
5 out of 5 average rating, 35 reviews

Riverside Cabin in the Blueridge with 1GB internet

Relax with the whole family at our peaceful riverside cabin, nestled in the blue ridge mountains, surrounded by mountain trails, winery’s and brewery’s. With a large kitchen, smoker, BBQ, Blackstone grill, coffee maker and KitchenAid mixer all available, you have all the amenities of home, in the relaxing cabin on 8 acres. Enjoy the multiple large decks for outside dining or enjoying nature and the local wildlife as well as the waterfall fed Koi pond and soothing sounds of the rapidan river.

Superhost
A serene view of the cottage set beside a gently flowing creek. Lush greenery surrounds the property, with a large tree in the foreground. The home is partially visible, featuring a star decoration on the facade and a covered porch overlooking the landscape.
Cottage in Luray
4.84 out of 5 average rating, 119 reviews

Creekside Cottage at Shenandoah

Welcome to our secluded cottage in the woods overlooking Shenandoah National Park! Your home base is located 10 mins from the cute town of Luray, through idyllic farmland and on acres of private hillside forest along a relaxing creek. As you enter this 3br/2ba home, you’ll find cozy cottage charm with thoughtful updates and modern amenities complete with a private hot tub. Within ~20 mins you'll find: - Shenandoah NP entrance - Luray Caverns - Wine country - Canoeing the Shenandoah River

Top guest favorite
Three red Adirondack chairs are positioned in a grassy area overlooking a landscaped yard, with trees and bushes providing a natural backdrop. The soft glow of dusk casts a serene ambiance across the scene.
Home in Madison
5 out of 5 average rating, 72 reviews

Home with beautiful mountain and river views

Welcome to the Madison House! This custom designed and built estate rests on a knoll overlooking 13.5 private acres on the Robinson River in rural Madison County, VA. Views of the Blue Ridge Mountains and direct Robinson River frontage makes this property a perfect destination for all four seasons. The outdoor space is ideal for friends and family gatherings and is ideally located near restaurants, wineries and breweries. The indoor space is both spacious and cozy for ample relaxing.

Guest favorite
The image shows a quaint cottage with a small porch overlooking a serene landscape. A gentle stream flows alongside the property, surrounded by lush greenery and trees. The sky is bright with fluffy clouds, adding to the tranquil outdoor setting.
Farm stay in Sperryville
4.91 out of 5 average rating, 159 reviews

Carriage House @ Sharp Rock Winery at Old Rag Mtn

Join us at Sharp Rock Vineyards in our 1850 Carriage House, a cozy romantic one room cottage perfect for a couple, set above a rushing trout stream at the base of Old Rag Mountain. Enjoy the peace of a private setting only minutes from Shenandoah National Park and hiking at Old Rag and White Oak Canyon. We are 10 minutes from Sperryville and close to local wineries, breweries, and eateries. In the evening enjoy our riverside fire pit or the brilliant firefly display on summer nights.

Superhost
An open-plan kitchen and living area is showcased with wooden beams and large windows, allowing natural light to illuminate the space. A kitchenette features wooden cabinetry, a microwave, and a small dining bar with three tall stools. A rocking chair is positioned beside a window overlooking the woodland.
Farm stay in Brightwood
4.93 out of 5 average rating, 145 reviews

Robinson River Cabin - Tri Creek Farm

If you spend most of your career glued to a computer and other screens, this place is for you. TriCreek Farm is a place for you to disconnect, reboot, and fuel your soul. This riverfront cabin is situated on ~100 acres, over 1/2 mile of Robinson River frontage, with breathtaking views. There are creeks, fishing, and hiking trails to explore and enjoy. The cabin is located in Brightwood, Virginia, a small town located in Madison County between Culpeper and Charlottesville Virginia.

Top guest favorite
A view is presented through two large windows framed by white trim, showcasing serene lake and mountain scenery. A wooden duck figurine rests on the window sill, adding a touch of charm to the peaceful outdoor vista visible beyond the glass.
Guest suite in Ruckersville
4.97 out of 5 average rating, 174 reviews

Serenity Lakeview Cottage

Renovated lakefront apartment, downstairs from the main home. It is located on beautiful Greene Mountain Lake with year-round lake and mountain views. Wildlife on the lake includes geese, herons, ducks, osprey, eagles, turtles, and beavers. The setting is serene and peaceful. You will have a private entrance and a covered porch. Kayaks are available for your use on the lake. Unit approved with a Special Use Permit for Tourist Lodging by Greene County.

Guest favorite
A sweeping view of rolling hills and distant mountains is captured under a textured sky filled with soft clouds. Lush green fields extend in the foreground, lined with trees that provide a gentle contrast to the expansive landscape.
Loft in Madison
4.93 out of 5 average rating, 68 reviews

The Loft at Hebron Valley Overlook

Rest, Rewind & Relax while enjoying breathtaking Blue Ridge Mountain and Hebron Valley Views. Home features a king size bed, full bath, kitchenette, living room with queen sofa bed, dining room, sun room. Enjoy your morning coffee or evening cocktail on the outside deck while watching the evening sunset. Meander down to the river and walk the trails through the woods and or sit by the river or pond and enjoy the serenity and the sounds of nature.

Top guest favorite
The cabin exterior is surrounded by lush greenery, with a spacious covered porch featuring a wooden railing. Planters with flowers are visible at the front, while a well-maintained lawn leads to the entrance. A small outbuilding is located nearby among the trees.
Cabin in Stanardsville
5 out of 5 average rating, 124 reviews

Conway Cabin

Conway Cabin is an old hunting cabin that we have made into a comfortable and relaxing getaway. It is located at the foot of Lewis Mountain part of the Shenandoah Nation Park. National Hiking trails just up the road and Early Mountain Winery and Bald Top Brewery are 15 minutes away. Go out enjoy your day and come back and relax in the Conway River or on the large covered porch. STARTING SEPTEMBER 2025 FIREFLY WIFI WILL BE AVAILABLE AT CONWAY CABIN

Popular amenities for Madison County waterfront rentals