Vacation rentals in Madison County

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Top-rated vacation rentals in Madison County

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Guest favorite

Tiny home in Reva

4.94 out of 5 average rating, 326 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.

Guest favorite

Guesthouse in Orange

5 out of 5 average rating, 231 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.

Guest favorite

Rental unit in Madison

4.9 out of 5 average rating, 249 reviews

The Studio at Dark Run Retreat

Quiet studio on a secluded 5 acres only 3 miles from town. Kick back and relax by the pool in the warmer months, or in the hot tub in the cooler months. Small trails lead to the creek running along the property, maybe you'll even catch a glimpse of the deer or turkey that wander thru...we've even seen a lil bear once! There is an apartment above the studio, so we ask that you be mindful of those guests if occupied. *The studio got a make-over! As of 10/6/20, we will no longer be hosting pets*

Superhost

Home in Stanardsville

4.91 out of 5 average rating, 184 reviews

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.

Guest favorite

Cottage in Madison

4.91 out of 5 average rating, 163 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.

Guest favorite

Guesthouse in Syria

4.96 out of 5 average rating, 363 reviews

Little House on Strother Run

Nestled between Mount Tom and Double Top Mountain and at the edge of the Shenandoah National Forest, Little House is the perfect starting out and ending point for a peaceful and relaxing stay in the Appalachian Mountains. Little House is located at the edge of our 7 acre property. You'll enjoy the bucolic atmosphere of our farmette which includes use of our shared sitting area on Strother Run. The sitting area is shared with the main house which is rented or used by our family periodically.

Guest favorite

Cabin in Etlan

4.99 out of 5 average rating, 118 reviews

Cozy Mountain Cabin w/WiFi, TV, Fire Pit,Patio

This cozy getaway is located only minutes from Old Rag, White Oak Canyon, trout fishing, horseback riding, wineries, breweries, and more! Our A-frame cabin is a 400 sq ft space with all the modern amenities, a private patio with a stone fire pit, loft bedroom, and spacious bathroom. Unwind, relax, and enjoy some time at the beautiful mountains….a couples getaway, friends retreat, or vacay with the kiddos! Are your desired dates already booked? Check out our other listing, Bald Eagle Cabin

Guest favorite

Cottage in Orange

4.95 out of 5 average rating, 413 reviews

Private Fenced Yard for Dogs/Horses - 2BR Cottage

2BR Hen and Hound Cottage is located just outside Orange, VA and has a private fenced yard for pets and walk-in access to adjacent James Madison's Montpelier and its many walking trails. In addition, we are minutes away from all of the popular wedding venues in Orange and a short drive to Shenandoah National Park. Our house on Whistle Stop Farm (so named for the train that passes by) is next to the cottage if you need us. Otherwise, the place is yours. Come enjoy some time in country!

Guest favorite

Yurt in Etlan

4.95 out of 5 average rating, 213 reviews

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.

Superhost

Cottage in Stanardsville

4.85 out of 5 average rating, 138 reviews

Chateau Merlot

This cute, quiet, and cozy Appalachian Cabin has been lovingly renovated to provide a relaxing retreat into the mountains of Virginia. Enjoy the expansive and private back yard (great for stargazing!), nearby hiking trails, and abundant wineries in the area. Enjoy the wildlife that stops through to feed on the mature fruit trees, the mountain breeze, and the quiet solitude offered by slowing down and visiting the mountains. There is a small creek at the back of the property as well.

Guest favorite

Farm stay in Brightwood

4.96 out of 5 average rating, 122 reviews

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.

Guest favorite

Guest suite in Syria

4.97 out of 5 average rating, 224 reviews

❤️Old Rag Mountain Views on 70 Acres near SNP!

Enjoy expansive mountain views of Old Rag and the Shenandoah National Park from the guest suite of this private, custom built octagonal cabin nestled in 70 acres on the side of beautiful Doubletop Mountain. Nearby activities include hiking, wineries & breweries, horseback riding, trout fishing, and antiquing. Visit nearby Old Rag Mountain, Shenandoah National Park, Luray Caverns, White Oak Canyon, Charlottesville and Culpeper. Just two hours from Washington, DC.