Vacation rentals with outdoor seating in Madison County

Robinson River Roost - Cottage near Shenandoah NP

Enjoy a slice of country life in our rustic 3 BR, 1.5 bath cottage nestled along the Blue Ridge in Madison County. Great for a family or small group. Minutes to scenic hikes at White Oak and Old Rag in Shenandoah National Park, plus wineries, breweries and festivals at Graves Mountain Lodge. Steps away from trout fishing and swimming holes of the peaceful Robinson River, plus Possum's Store across the street. Convenient to Charlottesville, Culpeper, Blue Ridge Pkwy, Luray Caverns, Camp Varsity.

Log Cabin and Ragged Rock Ridge

Mountaintop log cabin nestled in a mature, tranquil forest with spectacular views, ideally located near adventures like hiking in Shenandoah National Park (including Old Rag & White Oak Canyon), many local wineries/breweries/distilleries and quaint towns of Sperryville & Madison, VA. The authentic log cabin includes a cozy stone fireplace, porch, and patio with Old Rag views. Ponds, wildlife and hiking also available on the sprawling 300-acre property. Escape to the Cabin at Ragged Rock Ridge.

Willie's Place Country Cottage Pets Allowed

Step out your front door and pet horses located next door. Willie's place is newly renovated and has all the amenities you need. Located close to wineries, shopping, wedding venues, Historic Montpelier, Corn Maze, Town of Orange, Woodberry Forest School, 10 minutes to Gordonsville, 30 minutes to Charlottesville. Kayak the Rapidan, take a horseback ride at Oakland Heights or see a play at Barboursville. Exposed beams throughout, a beautiful Loft and back porch for sitting. You won't go wrong.

The Tool Shed, Pet Friendly

The Tool Shed at Mountain Field Farm provides a delightful retreat just a short 20-minute drive from the majestic Old Rag Mountain and the serene White Oak Falls. Immerse yourself in the breathtaking landscape, explore the nearby exquisite wineries and craft breweries, and meander through the quaint streets of Culpeper, where adventure blends seamlessly with relaxation and fine dining. Don’t forget to bring along some peppermints for our gentle horses, who are always eager to greet visitors.

10-Acre Dog-Friendly House w Grill & Near Wineries

Welcome to the Reva Retreat! This country house sits on 10 acres, nestled between Shenandoah Nat'l Park & the Blue Ridge Mtns, with wineries and breweries nearby. Approx 1.5 hours from DC and 45 mins from Charlottesville makes this the perfect getaway destination to escape the city & unplug. Stocked with amenities: BBQ grill, dine al fresco, stargaze by the firepit, cook a feast in the new kitchen, play board games in the basement, or connect your laptop to a 32" monitor to work remotely.

Spacious Retreat with Outdoor Firepit & Large Deck

Enjoy this tucked-away spacious, peaceful family getaway with lots of indoor and outdoor space. Wooden cathedral ceilings with fireplace and lots of windows to enjoy nature. Dine outdoors on the large wrap around deck with grill, firepit, horseshoes, and cornhole. Enjoy fishing and the rope swing at the nearby Robinson river. Walking distance to Blue Quartz Brewery and Winery. Enjoy the best of Madison - Local Horseback Riding, Hiking Old Rag and White Oak Canyon all within minutes away.

One Of A Kind Home in VA Wine Country on 50 acres

Welcome to Lumusa Lodge. Leave your cares behind as you turn onto the windy road that leads you to this beautiful 50-acre retreat. We are proud to share our home and hope your time here is rejuvenating. Designed/built by a Hollywood actor and situated in wine country, this home is an hour from Dulles, 45 minutes from Charlottesville & 15 minutes from Culpeper. We have an adjacent farmhouse if you need additional space. Great venue for weddings, bachelorettes, and other special events.

Serendipity with a View. (cozy mountain retreat)

If you want relax with a quiet mountain view. WE HAVE STARLINK WIFI. Very little to no cell sevice. Serendipity is perfect place to reconnect with a family, group of friends, or romantic getaway ( Fire place inside, games, books) Fabulous view is Graves Mountain. Great hiking with the famous Whiteoak Canyon Trail and Old Rag Mountain Trail, just to name a few. Lots of local wineries to explore. Robinson River steps away for great trout fishing. Private pond access .25 away.

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.