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

The Log Cabin at Ridgeview - Hiking, Wine, UVA

Entire main floor of quaint log cabin in the heart of Virginia's Wine Country. Close to Charlottesville airport, UVa campus, Shenandoah National Park, wineries, breweries, local restaurants. NOTE: Prices shown are for 2 bedrooms, 1 queen and 1 double, and 2 baths. For access to 3rd bedroom, at an additional fee which includes one double and one single, set number of guests to 5 or 6. Access to laundry. Cozy front porch, tons of parking, screened in porch out back for dining or relaxing.

Fauna Haven: Farm-Estate and Animal Sanctuary

Tranquil Fauna Haven will help you regain sanity. Whether looking for a getaway or a hub for local sightseeing, look no further. Relax in a private guest house on 20 acres with pond & intimate hiking trails. 1 bedroom, plus curtain for sofa sleeper privacy. Full kitchen/laundry. Visit with our farm animals. 30 min. to UVA/Charlottesville, 38 min. to Monticello or Montpelier, 22 min. to Shenandoah Nat'l Park Swift Gap Entrance, numerous vineyards nearby. Great for 'littles' and adults alike!

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.

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.

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.

Luxury Tiny Home 2: Sauna, Farm & Mountain Views

Welcome to Rooted Land Co., a 350-acre private retreat nestled at the base of the Blue Ridge Mountains with over one mile of Rapidan River frontage. The property features three luxury tiny cottages, each intentionally positioned for privacy and stunning mountain views. Guests are invited to enjoy hiking, fishing, wildlife observation, and farm life in a serene, rural setting just minutes from Virginia’s finest wineries, breweries, and Shenandoah National Park.

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.

Finks-Johnson House on Strother Run

The Finks-Johnson House on Strother Run is a renovated farmhouse built by the Finks Family @1900. We have 3 bedrooms, 2.5 baths, a fully equipped kitchen, den, living room and front porch with swing and rockers!! Our property extends across the road, where there is a sitting area above Strother Run. The "sitting area" on Strother Run is shared with the "Little House," at the back of our property, which is rented as well.

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

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!