Holiday rentals with outdoor seating in Madison County

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).

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.

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.

New, 5BD/4BA | hot tub, arcade, pool table, views

Welcome to this new, 2,880 sf LUXE retreat in Shenandoah Woods--a spacious cabin designed for unforgettable getaways. It features 5 king beds, 4 full baths (2 en suite, 1 adjoining, 1 hall), and stunning views from the porches, hot tub, and rooms. More highlights: ★Arcade, board games, 6 ft pool table ★Fire pit ★Elect fireplace ★Elect Grill on deck ★Smart TVs up to 70" ★Fast WiFi ★Dining for 10 ★Well-equipped kitchen ★5 mins-Stanley ★13-15 mins-Luray Caverns ★25 mins-Shenandoah National Park

Farm Cottage just outside town of Orange.

Charming 1920's cottage on a large farm just outside the town of Orange. Completely renovated and updated. Convenient to vineyards, battlefields, wedding venues and popular tourist destinations. Bucolic setting, very private. Spaces to enjoy the out of doors. Less than 2 miles to in-town wedding venues and Rounton Farm. Less than 4 miles to Inn at Willow Grove. 5 miles to Montpelier. Less than 7 miles to Grelen. 10 miles to Gordonsville. 12 miles to Barboursville. 19 miles to Mineral.

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.

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!

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.

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.

Charming Chalet in Blue Ridge Wine Country

NEW! PICKLEBALL/BASKETBALL COURT PUTT PUTT GOLF Sunset Ridge is in the heart of all you want to do! Newlyweds to families, everyone will love it here! The peace and quiet of the country, or the excitement of exploring new and different places, all await you! Check out our guidebook for local attractions, restaurants, nightlife, and sightseeing. Enjoy the serenity of the country! Follow us: @sunsetridgechalet