Vacation rentals in Madison

Spectacular Mountain Retreat

Cottage is the guest house of our country home. Situated on a mountain with spectacular views of the Blue Ridge and access to many hiking trails; biking; fishing and swimming in private pond only steps from the door. Cottage is located within easy driving distance of multiple wineries, Sky Line Drive and Shenandoah National Park; Montpelier; and restaurants and shops. We can accommodate no more than one dog, with prior permission. In April 2023, we again upgraded our internet (see below).

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.

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.

Relaxing 2BR CABIN, 12 acres, dog friendly, hiking

Bring the whole fur family & enjoy precious time away from the hustle & bustle of everyday life. This updated cabin sits on 12.5 acres of mainly wooded land in the heart of the blue ridge- Madison County. Within 30 minutes of wineries, breweries, hiking, & Charlottesville! Boasting a primary loft bedroom w/ a queen bed and a bonus room w/ a full bed, this home away from home can comfortably sleep 4-5! Front porch swing & fenced yard for the pups to play. Guests can completely relax!

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.

Mountain Cabin Getaway w/WiFi, TV, Fire Pit, Patio

This unique, modern A Frame cabin is located at the foothills of The Shenandoah Mountains only minutes from Old Rag Mountain, White Oak Canyon, trout fishing, horseback riding, wineries, breweries, and more! This 400 sq ft. tiny home has all the modern amenities you need to feel right at home. Step outside, enjoy the mountain air, and relax on your private patio with a cozy,private fire. Are your desired dates already booked? Check out our other listing, Black Bear Cabin!

CloudPointe Retreat

Rare Appalachian Treehouse Gem! Luxurious, one-of-a-kind retreat for couples. Elevated tiny house among the treetops, private parking, plush bedroom, sleek bathroom, beautiful kitchenette, loveseat, lounge, private double-level decks, fireside lounging (wood provided), gas grill, and patio with a hot tub! Surrounded by nature, with wineries, hikes, restaurants and shopping all nearby. Please come and relax and revel in the beauty of nature! 4WD is recommended.

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! 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.

The Cabin at the Lake

Lake view cabin! 2 bedrooms one bathroom. Close to breweries, wineries, grocery store, and 20 minutes from Shenandoah National Park. You will have everything you need at our home provided for you. We have a canoe and row boat for you to venture out on the water and fishing poles, just bring your tackle, bait and bathing suit! We have high speed internet (100+mbps) at the cabin and a smart Tv! No parties!

Luxury Mountain Tiny Home #2: Sauna, River, Views

Escape to a private 350-acre farm at the base of the Blue Ridge Mountains—just minutes from Shenandoah National Park. Designed with couples in mind, this luxury tiny home offers complete privacy, mountain views, a private sauna, and direct access to the Rapidan River. Whether you're celebrating something special or simply stepping away, this is a place to slow down and reconnect.

Madison Farmette Guest House

Early Mountain Vineyards is a little over a mile from our place. We are minutes from the SNP trails and Bald Top Brewery. Enjoy this private getaway that is convenient to hiking, wine tours, art workshop weekends, biking, hot air ballooning, antiquing, all in a genuinely welcoming community that offers a great lifestyle.

Lucian's Place

Relax with the whole family, friends, or yourself at this peaceful home. This house has history and character to it. It's surrounded by rolling hills, wineries and rivers. If you are looking to unplug or get away for some star gazing and bonfires you’re at the right place. It's newly renovated and looking for stays!