Holiday rentals with a fireplace in Madison County

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.

New~5BD/4BA~Upscale~Arcade~LL

★New LUXE cabin, new build, A+ views, 2880 sf ★5 king bedrooms, 4 full baths (2 en suite, 1 adjoining, 1 hall) ★In Shenandoah Woods ★Arcade & board games, books, 6 ft pool table ★Porches & hot tub overlooking valley & mountains ★Fire pit ★Electric outdoor grill ★Fireplace (elect.) ★Smart TVs (incl. a 70") ★Fast WiFi ★Dining for up to 10 people (with extension) ★Firewood provided for fire pit ★Well-equipped kitchen ★5 mins-Stanley ★13-15 mins-Luray/Luray Caverns ★25 mins-Shenandoah National Park

Rustic Farmhouse on Farm W/ Mountain & River 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.

Log Cabin at 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.

Creekside Cottage Near Hiking

Creekside Cottage is the perfect getaway home to escape to the beautiful Blue Ridge Mountains. This newly renovated luxury cottage is only minutes from hiking trails and just a short drive from the Old Rag trailhead. Nestled in Syria, Virginia, this comfortable space features updated amenities such as a rain shower, a well appointed kitchen, plenty of lounge spaces, board games for days, and a central wood burning stove. Just a few steps out the back door you'll find your own private creek.

Peaceful Secluded Old Rag Retreat

The spacious one bedroom yurt is located high on a forested hillside in the middle of 15+ acres. Come enjoy a natural and serene getaway with all the comforts of home- a full kitchen (ie, all utensils, setting for four), a bathroom with shower and laundry, a queen bedroom, and a queen foldout sofa in the living room by the wood burning stove. The windows roll up from the outside and have permanent screens inside. There is also a BBQ grill, a separate firepit, and WiFi via satellite.

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.

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.

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.

Modern Cabin | Old Rag in Shenandoah National Park

Stay near the best mountain trails in Shenandoah National Park with a few wineries and breweries close by. You'll have access to ... -- Our private creek and swimming hole -- A hot tub under the stars -- Starlink WiFi with up to 200 Mbps download speeds, adequate for remote work and streaming services (see more below) -- A kitchen fully stocked with all the equipment you'll need to prepare your own meals -- 2 bedrooms and an inflatable mattress in the common area

Stunning Modern Cabin w WiFi near Shenandoah Park

My family lovingly restored this log cabin and it was recently featured in the Washingtonian as one of the top places to visit in the DC region! We’re so excited to share it with you! It is one of the only houses in the area with reliable high speed xfinity wifi. It is a short drive to so many of the popular Shenandoah National Park hikes and it's centrally located to so many of the popular breweries, wineries, restaurants, and adorable small towns.

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