Holiday rentals in Madison

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

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).

Robinson River Roost - Cottage near Shenandoah NP

Enjoy a slice of country life in our rustic 2 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 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.

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.

Brewery Manor Sleeps 10 Hot Tub

Woodbourne Estate, circa 1810, is a National and Virginia historic registered landmark Manor House and farm nestled in the foothills of the Blue Ridge Mountains in Madison, Virginia. The 53-acre Estate is also home to our award-winning Bald Top Brewing Company which sits just a comfortable stroll beyond the Manor house. This magical Manor, with its gorgeous grounds, gardens, barns, ruins, pool, stream and vistas awaits! The Manor at Bald Top: Drink in the Moment!

Charming Guest Cottage at Winery

Early Mountain Vineyards' charming Guest Cottage, nestled next to our front block of grapevines and below our historic hilltop barn, offers breath-taking views of the Blue Ridge Mountains and a serene place to watch the sunset while sipping wine. Only short distance to our Tasting Room - open 5 days a week, Thursday - Monday. We recommend a reservation in advance - this can be made via our website, Early Mountain Vineyards, or by calling our winery directly.

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!

Unique Mountain Getaway: WiFi, TV, Fire Pit, Patio

This unique, modern cabin is located 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 and relax on your private patio with a cozy fire and s’mores. Are your desired dates already booked? Check out our other listing, Black Bear Cabin!