Vacation rentals in Madison County

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Madison County

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

Guest favorite

Guesthouse in Orange

5.0 out of 5 average rating, 175 reviews

Taj Garage Guesthouse

Newly constructed (2021) above garage guesthouse with private, self check-in entrance, off-street parking, located among historic homes just 4 blocks to restaurants, shops, park and art galleries in downtown Orange. Guesthouse includes a fully equipped kitchen, queen bed, full bath, seating area, TV, wifi and balcony. Handcrafted heart pine furniture. Level 2 EV Charger. Kitchen includes refrig, stove, microwave, toaster and Keurig. Close to superb wineries, breweries and historic sites.

Aug 5 – 12

$102 per night
Guest favorite

Tiny home in Reva

4.94 out of 5 average rating, 287 reviews

K-9 Heaven Dogs Run Free

K-9 Heaven ... Get away from the City. Enjoy clean open spaces. Spend time with the horses.They love peppermints. Don't leave your K-9 family at home, It's there vacation too. 100% off leash 20 min away Old Rag Mountain , White Oak Falls and downtown Culpeper. There are so many trails for a wonderful hiking experience. We are with in 10 min of nearby winerys, breweries We are off leash for dogs . Never leave the farm as we have Doordash to bring you whatever you desire, Wine, food anything.

Apr 16 – 23

$109 per night
Guest favorite

Cottage in Madison

4.9 out of 5 average rating, 135 reviews

Robinson River Roost - Cottage near Shenandoah NP

Enjoy a slice of country life in our rustic 3 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.

May 7 – 14

$105 per night

Popular amenities for Madison County vacation rentals

Other great vacation rentals in Madison County

Guest favorite

Guest suite in Stanley

4.98 out of 5 average rating, 158 reviews

Tranquility in the Mountains

Aug 20 – 27

$106 per night
Guest favorite

Guest suite in Syria

4.96 out of 5 average rating, 198 reviews

❤️Old Rag Mountain Views on 70 Acres near SNP!

Jul 6 – 13

$111 per night
Guest favorite

Cottage in Etlan

4.97 out of 5 average rating, 159 reviews

Amy's Place

Apr 2 – 9

$124 per night
Guest favorite

Cabin in Ruckersville

4.93 out of 5 average rating, 359 reviews

Mountain View’s cabin!

Jun 13 – 20

$85 per night
Guest favorite

Guest suite in Ruckersville

4.98 out of 5 average rating, 134 reviews

Serenity Lakeview Cottage

Jun 18 – 25

$102 per night
Guest favorite

Farm stay in Sperryville

4.98 out of 5 average rating, 120 reviews

The Roost at Upper Nonesuch

Jun 14 – 21

$122 per night
Superhost

Cabin in Rochelle

4.84 out of 5 average rating, 375 reviews

Pop's Place on the Rapidan River.

Nov 27 – Dec 4

$77 per night
Guest favorite

Cottage in Madison

4.98 out of 5 average rating, 123 reviews

Fishback Cottage, Central location

Aug 28 – Sep 4

$176 per night
Guest favorite

Bungalow in Orange

4.98 out of 5 average rating, 357 reviews

Farm Cottage just outside town of Orange.

Feb 1 – 8

$125 per night
Superhost

Guest suite in Madison

4.83 out of 5 average rating, 208 reviews

Farmette in Madison - Madison, VA

Dec 6 – 13

$76 per night
Guest favorite

Farm stay in Brightwood

4.97 out of 5 average rating, 87 reviews

Robinson River Cabin - Tri Creek Farm

Jan 1 – 8

$116 per night
Superhost

Home in Madison

5.0 out of 5 average rating, 4 reviews

Haywood Haven

Oct 3 – 10

$118 per night

Destinations to explore