Vacation rentals with a kayak in Madison County

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.

log cabin on the river(3 acres w/pond)kayaks+

Relaxing log cabin riverfront get away on the Shenandoah river. Enjoy tubing, kayaking and fishing right in the backyard. Sit on the screened-in porch to read a book, enjoy a meal or play a board game with your family. 20 minute drive to Massanutten Resort where you can enjoy skiing, mountain biking and an indoor waterpark. 30 mins to James Madison University and 25 mins to the Swift Run entrance to Shenandoah national park. We hope your family enjoys our house as much as we do.

Peaceful River Retreat: Hot Tub, Kayaks & Fire Pit

*Included -4 kayaks & 1 canoe- direct access to private river front use** Perched on 2 acres of riverfront property with over 200 ft of private shoreline on river rapids. Peaceful River has 2 comfortable king, and 2 twin beds and all the furnishings you'll need to enjoy your stay - updated kitchen, spacious screened-in porch, 2 updated full baths, and a separate riverside hot tub area. The wildlife is abundant and the views are peaceful. Enjoy relaxing & exploring as your worries float away.

Tugboat/Private Lake - Farm Animals - Fish, Swim,

Get swept away to a Magical Tug/Houseboat! Newly renovated with all modern conveniences, incl. fully stocked kitchen, full bathroom, AC, heat, & WiFi. Tug floats on an 8 acre private Lake w/ Island on 142 Wooded Acres, with 5+miles of hiking/biking trails. Enjoy Swimming, Kayaking, SUP, Fishing, Hiking, Biking, Exploring, or just relax on your own beach by the fire pit. Visit farm animals just a short walk around the lake...Theo the Cow, Sheep, goats, turkey, ducks, chickens, and rabbits.

Cottage at Frog Jump- woodland privacy at its best

Guesthouse ideal for two people. Small cottage (1 bed, 1 bath) is situated in a country setting on ten wooded acres along a large serene pond. It features a darling kitchenette with sink, fridge, microwave and toaster/convection oven. (No stove top, no oven.) You'll enjoy birdsong and views of various wildlife. A quiet, restful place to stay when you want to be near Shenandoah Nat’l Park, UVA, Charlottesville, Virginia wineries, Monticello, Montpelier, CHO, and other close-by attractions.

TreeTop at Mt Run Lake (Private Guest Apartment)

Spacious one bedroom guest apartment with SEPARATE ENTRANCE, private separate patio and reserved parking in this newly decorated full apartment, set on four acres with lakefront views situated in the foothills of the Blue Ridge Mountains. One flight of stairs up to a beautiful apartment with fantastic views of the lake and surrounding property. Private and secluded yet only 10 minutes from Historic downtown Culpeper with its many restaurants, local shops, grocery stores and pharmacies.

Garden Oasis outdoor entertainment at FrogPointe.

Nestled in between The Plains and Middleburg, this charming cottage is ready to help you relax. Perfect for family and friends during horse events nearby, like Gold Cup, Middleburg Film Festival, Christmas in Middleburg, Twighlight Polo, and much more. Fully functional kitchen with all you could need to cook a meal, fully furnished, indoor and outdoor dining, two large modern bathrooms, and internet / movies for a calm night in. This property stands out for its limitless outside fun!

Modern Riverfront Cabin w/ HotTub, FirePit, Kayaks

Welcome to Skyview River Retreat! Tucked along the tranquil South Fork of the Shenandoah River, this cozy cabin invites you to slow down and soak in the beauty of nature. Spend your days paddling in one of the kayaks or canoe, then unwind in the hot tub in the evenings, gather around the fire pit to roast s’mores, or head inside to enjoy the full arcade room. With a fully stocked kitchen and high-speed internet, you'll enjoy the perfect mix of rustic charm and everyday conveniences.

Rustic River Retreat- 2 Bedroom Riverfront Lodging

Peaceful nature and fun adventures await at this riverfront ground floor retreat. Open floor plan, full kitchen, two bedroom, 1 bath. Beautiful lot right on the Shenandoah river. fishing, canoeing, kayaking or just kick back by the fire and relax. 15 minutes from Massanutten Resort, 15 minutes from Skyline Dr., the Appalachian trail and 15 seconds from the Shenandoah river. Many wineries and breweries in the vicinity. A great place to make wonderful memories. Owner on premises.