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Vacation rentals in Madison County

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Top-rated vacation rentals in Madison County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Superhost
Home in Madison
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. New 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. Pet (dogs only) $30 per night.
$131 per night
Superhost
Home in Brightwood
Hilltop Haven Luxury lodging in Wine country
If you want to feel pampered, Hilltop Haven is the place for you! It is a beautifully decorated SECOND STORY apartment where you can enjoy a towel warmer, heated toilet seat, a bed fan that blows cool air between the sheets of the gigantic king size bed, private balcony, private fire pit, jetted bathtub, reading nook and electric fireplace. There are breakfast items available for you to prepare such as muffin mixes & pancake mix as well as a variety of snacks and drinks
$110 per night
Superhost
Guesthouse in Madison
Hebron Valley Cottage
Nestled in the scenic Hebron Valley, this 2 bedroom 1 bath cottage is the perfect getaway from busy, city life. The cottage offers panoramic views of the Blue Ridge Mountains, including Old Rag and is located near several wineries, breweries, restaurants, antique shops, hiking trails and historic sites. The cottage is 3 miles from the town of Madison and is convenient to Charlottesville, Culpeper and Orange.
$135 per night

Other great vacation rentals in Madison County

Superhost
Guesthouse in Boston
The Bunkhouse- simple & serene w/mountain views
$150 per night
Superhost
Cabin in Etlan
Modern Cabin | Old Rag in Shenandoah National Park
$232 per night
Superhost
Bungalow in Rochelle
Blue Ridge Bungalow~Mountain Views~Cozy Fireplace
$155 per night
Superhost
Guesthouse in Syria
Little House on Strother Run
$89 per night
Superhost
Guesthouse in Orange
Taj Garage Guesthouse
$128 per night
Superhost
Farm stay in Sperryville
The Roost at Upper Nonesuch
$135 per night
Superhost
Cottage in Etlan
Amy's Place
$165 per night
Superhost
Cottage in Madison
Fishback Cottage, Central location
$191 per night
Superhost
Home in Montpelier Station
The Cottage At Liberty Mill. Pets allowed $25
$175 per night
Superhost
Guest suite in Syria
❤️Old Rag Mountain Views on 70 Acres near SNP!
$114 per night
Superhost
Cabin in Madison
The Cabin at the Lake
$135 per night
Superhost
Farm stay in Hood
Firnew Studio
$172 per night

Destinations to explore