Cottage holiday rentals in Madison County

Find and book unique cottages on Airbnb

Top-rated cottage rentals in Madison County

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

0 of 0 items showing

1 of 3 pages

Guest favourite

Cottage in Madison

4.91 out of 5 average rating, 140 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.

22–29 Sep

€ 133 per night

Guest favourite

Cottage in Madison

5.0 out of 5 average rating, 11 reviews

Hebron Valley Sunsets Cottage

Two bedroom cottage with front porch and panoramic views of the beautiful Blue Ridge mountains. The Cottage is perfect for a family of four or two couples looking to get away for a weekend of outdoor adventures. The space is furnished with two queen size beds, comfortable living room furniture and tables for indoor and outdoor dining. The bathroom is spacious with dual shower heads and ample room . The kitchen is modern and fully equipped to service all your food preparation and cooking needs.

12–19 Feb

€ 295 per night

Guest favourite

Cottage in Madison

4.98 out of 5 average rating, 128 reviews

Fishback Cottage, Central location

Conveniently located in beautiful countryside of Madison, VA. With easy access to route 29 and centrally located to local breweries, wineries and hiking. Free fast wifi makes it easy for a business trip or for a night of relaxation with Netflix. Local places to visit include Bald Top Brewing Company, Early Mountain Vineyards, Prince Michel Vineyard, Yoder's Country Market, Piedmont Deli, Shenandoah National Park and Graves Mtn Farms. An easy 25-30 minute drive to Charlottesville or Culpeper.

22–29 Dec

€ 217 per night

Guest favourite

Cottage in Stanardsville

4.99 out of 5 average rating, 208 reviews

The Birds Nest Cottage

Our home is a newly renovated charming cottage nestled in the foothills of the beautiful Virginia Blueridge Mountains. You'll enjoy old cottage charm with added modern but classic updates to the entire home. Relax on the screened in back porch with tranquil sound of a water feature . Our home is centrally located near several beloved attractions like Skyline drive, Charlottesville, Massanutten Ski Resort, wineries and antique shops. Greenehills Country Club is directly across from our home.

1–8 Oct

€ 209 per night

Guest favourite

Cottage in Orange

4.91 out of 5 average rating, 131 reviews

Willie's Place Country Cottage Pets Allowed

Step out your front door and pet horses located next door. Willie's place is newly renovated and has all the amenities you need. Located close to wineries, shopping, wedding venues, Historic Montpelier, Corn Maze, Town of Orange, Woodberry Forest School, 10 minutes to Gordonsville, 30 minutes to Charlottesville. Kayak the Rapidan, take a horseback ride at Oakland Heights or see a play at Barboursville. Exposed beams throughout, a beautiful Loft and back porch for sitting. You won't go wrong.

19–26 Nov

€ 188 per night

Guest favourite

Cottage in Madison

4.94 out of 5 average rating, 113 reviews

Creekside Cottage Near Hiking

Creekside Cottage is the perfect getaway home to escape to the beautiful Blue Ridge Mountains. This newly renovated luxury cottage is only minutes from hiking trails and just a short drive from the Old Rag trailhead. Nestled in Syria, Virginia, this comfortable space features updated amenities such as a rain shower, a well appointed kitchen, plenty of lounge spaces, board games for days, and a central wood burning stove. Just a few steps out the back door you'll find your own private creek.

31 Oct – 7 Nov

€ 310 per night

Guest favourite

Cottage in Madison

4.93 out of 5 average rating, 68 reviews

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 one or two dogs with prior permission. In April 2023, we again upgraded our internet (see below).

1–8 Dec

€ 176 per night

Guest favourite

Cottage in Orange

4.95 out of 5 average rating, 367 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!

12–19 Jan

€ 116 per night

Guest favourite

Cottage in Syria

4.91 out of 5 average rating, 243 reviews

The Old Church Cottage~Old Rag,Kitchen,Grill, WiFi

Enjoy the Shenandoah Valley and Shenandoah National Park with us! Minutes from popular hiking trails, rivers and Graves Mountain Lodge, our Cottage is ideally situated to enjoy the local culture and festivals. If you're in the mood, DuCard Winery, Revalation Winery and Bald Top Brewery are nearby. When staying at The Old Church Cottage, you can relax in our hammock, grill in the back yard, fish in the nearby Rapidan or Rose Rivers or hike the Old Rag, White Oak and other close trails.

4–11 Feb

€ 183 per night

Guest favourite

Cottage in Leon

4.97 out of 5 average rating, 63 reviews

Relax Near Shenandoah NP, Hiking, & Wineries

Cottage at Grateful View is conveniently located in beautiful Madison Co. Accessible to Rt 29 and centrally located to local breweries, wineries (across from Prince Michel), and hiking. A few local places to visit include: Bald Top Brewing Company, Early Mountain Vineyard, the Skyline Drive in Shenandoah National Park (Old Rag Mtn and White Oak Falls). An easy 15-minute drive to Culpeper or 35-minute drive to Charlottesville with historical sites, restaurants, and antique shops not far.

8–15 Mar

€ 224 per night

Superhost

Cottage in Stanardsville

4.86 out of 5 average rating, 113 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.

1–8 Jul

€ 118 per night

Guest favourite

Cottage in Culpeper

5.0 out of 5 average rating, 46 reviews

Perfect and Easy "Get A Way " to Rare Air Farm!

At Little Red Hen Cottage, relax & recharge. Outside, walk 20 acres of rolling hills that host an active fruit & vegetable farm or sit by the Chimenea & star watch at night. This cottage is an easy drive from multiple vineyards, breweries & hiking trails (including Old Rag) tucked between Culpeper & Madison, Va. Once you're done with exploring for the day, return to all the amenties and comforts of home in a peaceful farm setting. Come and take in the quiet of Rare Air Farm!

8–15 Aug

€ 156 per night