House holiday rentals in Madison County

4.94 out of 5 average rating, 119 reviews

Designer cabin in the woods at Shennadoah NP

Come relax at our scandi inspired cabin in the woods. Five acres of pristine woods are the perfect backdrop for our renovated house, making it an ideal weekend retreat away from the busy city life. Discover the best spots in the area, including wineries and breweries, caverns and trails, antique shops and local makers, only a few miles from the house. Whether you are looking for a restful getaway, a source of inspiration, or a place to stay while you discover Virginia, this is the place for you.

4.92 out of 5 average rating, 124 reviews

Robinson River Retreat - Near River, SNP & Graves

Great location near the Blue Ridge Mountains in Madison County for family or friends. 3 BR, 2 BA spacious house. Property continues across street to the peaceful Robinson River for swimming or fishing. Minutes to scenic trails at White Oak Canyon/Cedar Run and Old Rag in Shenandoah National Park. Many wineries and breweries are near by as well as seasonal festivals at Graves Mountain Lodge. Convenient to Culpeper and Charlottesville. Fiber Internet with 140 Mbps upload & download; 30 ms Latency

4.98 out of 5 average rating, 310 reviews

Home in Hood

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.

Home in Montpelier Station

4.93 out of 5 average rating, 529 reviews

The Cottage At Liberty Mill. Pets allowed $25

Brand new charming cabin with views of the Blue Ridge Mountains. Two bedrooms, Loft with 2 twin beds, two large bathrooms and a spacious common area. Exposed chestnut beams, working gas fireplace make this cabin a perfect getaway. All the amenities you could want. Located minutes from James Madisons' Montpelier, 5 minutes from Historic Orange, 30 minutes to Charlottesville, 20 minutes to Culpeper and less than 2 hours to Washington, DC. A loft area with 2 twin beds. Great for kids. Beautiful.

4.9 out of 5 average rating, 220 reviews

Home in Stanardsville

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.

4.99 out of 5 average rating, 143 reviews

Home in Banco

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.

4.98 out of 5 average rating, 106 reviews

Home in Sperryville

Walk to Old Rag/Shenandoah*Hot tub* dogs welcome

Make some memories at this unique and family and dog-friendly place. Relax in the hot tub after hiking Old Rag. This rustic redone farmhouse with modern amenities is a short walk to the trailhead for the hike up Old Rag, a short walk to Hughes River fishing, and a short drive to Sperryville, historic Madison, wineries, breweries and other Shenandoah National Park hikes. The house is surrounded by acres of fenced open space, with a front porch, deck, weber gas grill, and 360 Mountain Views.

4.96 out of 5 average rating, 157 reviews

Home in Boston

Peacefield - Blue Ridge views near Culpeper

Welcome to the Peacefield! This retreat is nestled in the rolling foothills of the Blue Ridge Mountains in the shadow of Old Rag, overlooking Hazel River Farm (160 acres). The spacious estate is perfect for escaping the city. There are many options for relaxing with a deck, hot tub, pool (summer only), home theater, and an open kitchen connecting the dining and family rooms. The beauty of the estate includes walking trails, glimpses of sheep, and local art (watercolor and photography).

4.93 out of 5 average rating, 234 reviews

Home in Robertson

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.

4.96 out of 5 average rating, 169 reviews

Spacious Shenandoah Home on 35 Private Acres

Sitting on 35 acres of private land to be explored, this classic countryside vacation rental ticks all the boxes for a relaxing outdoors-geared getaway! You can practically picture yourself enjoying a glass of wine after a long day of exploring the natural beauty of Virginia from this perched hillside home, sporting a long private drive, and an expansive furnished deck. This 2-bed, 2.5-bath outdoors oasis is sure to have everyone unplugged, outside and enjoying living in the moment.

4.95 out of 5 average rating, 432 reviews

Unit A-Mountain Retreat- SAUNA-Hiking-Wineries

Renovated duplex in Madison, VA. Enjoy a peaceful setting, amazing views and convenient to wineries, wedding venues & hiking. SAUNA! On-site walking trail. Near Early Mtn Vineyards, Prince Michelle Winery, Yoder's Market, Bald Top Brewing & Plow & Hearth. A 30 min drive to Charlottesville, Shenandoah Nat. Park, Culpeper & Orange. Shopping, restaurants, breweries, antiquing, site seeing and more. *RENT ENTIRE HOME* - Inquire for our unit A & B combined rate. Dogs allowed-$30 fee.