Vacation rentals with a kayak in Madison County

River Front Mountain Views (Old Rag, SNP)

Relax with the whole family in this serene setting along a native brook trout stream where nature's sounds prevail. Most every room has wonderful views of the Hazel River and the Appalachian Mountains (Shenandoah NP) beyond. The river's clear waters invite fly fishing, and swimming holes abound as do nearby hiking trails in SNP (favorites, Old Rag and Marys Rock). Noted restaurants are nearby as are many vineyards and antique stores. (County code encourages multi-day [weekly/monthly] stays).

Outdoor spaces · Location · Cleanliness

Rustic Forest Cabin – Close to Shenandoah Park

Come unwind at this peaceful camping cabin, tucked away on a stunning 600-acre property made for slowing down. Wander over 10 miles of private hiking trails, paddle a canoe across one of our 4 quiet lakes, or stroll 4 miles of riverfront trails as the sunlight filters through beautiful oak forests. Don't miss our legendary 200-year-old tree — a true must-see. Whether you're traveling with family, friends, or your furry companion, this cabin is the perfect home base for making memories in nature.

Location · Value · Pets

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.

Outdoor spaces · Location · Checkout

Triquetra Farm: A Shenandoah Conservation Retreat

Immerse yourself in the charm of the Shenandoah foothills. Vineyards, history, and tranquil countryside await. 20 minutes from Shenandoah NP The apartment accommodates four adults on a working farm with abundant wildlife. Enjoy views of the fields and mountains from the elevated deck, fish in a 2-acre lake, or roam 110 acres of forest. The area is home to wineries, a farm brewery, and SNP. History is nearby, featuring the homes of three presidents and UVA. Come & recharge. @triquetrafarmrental

Outdoor spaces · Location · Hospitality

Guest Cottage @ South River Farm

Escape to the serenity of South River Farm, nestled in the picturesque Virginia Piedmont. Only 15 min to Shenandoah National Park, our charming studio cottage boasts a luxurious king-sized bed, chic new furnishings, cozy en-suite bathroom, and state-of-the-art appliances, ensuring a relaxing stay. As our guest, revel in the expanse of our working farm: roam miles of bucolic trails, relax by a stocked pond (no license needed), or fish in our stocked trout stream. Welcome to your rural retreat!

Outdoor spaces · Location · Hiking

Woodsy lakefront cabin with hot tub (near SNP)

Enjoy a romantic and peaceful getaway for long stays in the beautiful woods near Shenandoah National Park. This is my primary home and I adore it. You can pass your time by sitting by the lake, relaxing in the hot tub, drinking at the brewery (Bald Top) or the winery (Early Mountain) that are both down the road, or hiking in the national park (the closest entrance is about 20 minutes away). I hope you find a moment to be peaceful and still with the beauty and wildlife that surrounds you.

Location · Quiet · Kitchen

Pondside Retreat w/ Fire Pit, Fishing & SNP

Wake up to pond views just 15 minutes from Shenandoah National Park. Stroll 6+ private acres, cast a line, or sip coffee as deer wander nearby What you’ll love: 🛌 4 roomy bedrooms, 8 beds—ideal for families & groups 🔥 Fire pit on serene patio overlooking the pond 👨🏻‍🍳 Fully stocked kitchen & grill ✨Fast Wi-Fi + workspace After a day of hitting the trails and sipping wine, gather for games in the great-room, then fall asleep to frog songs across the water. Book your relaxing stay today!

Outdoor spaces · Location · Cleanliness

Stone Bridge Farm - 1 BR Riverfront ADA Apartment

This private apartment is part of a historic 1882 riverfront estate, offering comfort, accessibility, and peaceful surroundings. Ideal for solo travelers, couples, extended stays, or guests attending events nearby who want independence and ease of access. * Private entrance and parking * Kitchenette and sitting area * Designed to meet most ADA guidelines * Accessible bedroom, kitchenette and bathroom with transfer shower chair available * Quiet, private setting within a larger estate

Location · Hospitality · Hot tub

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.

Outdoor spaces · Location · Indoor spaces

The Skyhouse- simple & serene w/mountain views

Enjoy the solace and beauty of the Blue Ridge Mountains with modern and local comforts. Retreat and explore on this old 100acre farm- via foot- or float on the tiny pond in a kayak or SUP. Or venture out to Shenandoah National Park, the local coffee shops, eateries, wineries, and breweries. Whatever you choose the skyhouse is stocked with roasted coffee, farm-fresh eggs, fresh-baked bread, teas and soaps from our incredible local homesteaders and artisans.

Outdoor spaces · Value · Family

White Oak glamp tent #4. Safari tent, on a deck!

Come hike White Oak Canyon and then stargaze at the Big Dipper Ranch. Spend your whole time on our 23 acres or use it as home base as you explore all that Madison County has to offer. Old Rag and White Oak Canyon are minutes away as are wineries, breweries, orchards and much more. Critters big and small, we have them all! Please know we are in a remote area and wild animals and insects are part of nature and come with the camping experience!

Location · Outdoor spaces · Family

Stone Bridge Farm - 4 BR Riverfront House

This beautifully renovated 4-bedroom historic home, built in 1882, sits on 8 private acres with peaceful river access—perfect for families, wedding guests, retreats, and extended stays. Enjoy the charm of a classic Virginia estate with the comfort and convenience of modern updates, all while surrounded by nature. Note: The separate ADA apartment is not included in this listing but may be available separately.

Location · Outdoor spaces · Amenities