Cottage holiday rentals in Madison County

Echo Creek Cottage

Echo Creek Cottage is a cozy, peaceful guesthouse in a beautiful setting on our farm in Madison County, VA. We’re a short drive from many popular trails in Shenandoah National Park including Old Rag, White Oak Canyon, and Dark Hollow Falls. There are numerous wineries and breweries nearby including Early Mountain, Revelation, Shotwell Run, and Bald Top. The cottage is located between Sperryville and Madison and is centrally located to Charlottesville & Culpeper. We look forward to welcoming you!

Location · Family · View

The Cozy Conway Cottage

Enjoy peace and quiet along the Conway River. This relaxing getaway is about 1/4 mile off of rte 230. The cottage was an original one-room cabin with a centrally located wood stove/fireplace. It now boasts 2 bedrooms, 1 bathroom, a full kitchen, large windows and a patio/deck with river views. During the fall and winter months, you can see the sunset over the mountains of the National park. It’s a 20 min drive to the Shenandoah National Park entrance and 5 minutes from Early Mountain Vineyard.

Value · Family · Nearby

Chateau Merlot

This cute and peaceful Appalachian Cabin vacation rental has been lovingly renovated to provide a quaint retreat into the mountains of Virginia. Explore 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.

Value · Family · Accuracy

Sister's View

A refurbished 1950's country cottage, adjacent to 80 beautiful acres, overlooks the Blue Ridge Mountains. The house has high-speed internet. Enjoy an amazing sunrise while sitting on your bedroom deck sipping coffee. View sunsets from the front porch with a glass of wine purchased from local vineyards. Whether visiting UVa, hiking in the Blue Ridge Mountains, touring the local wineries, craft breweries, or attending an event at the Barn at Edgewood - Sister's View will make your visit complete.

Family · Value · Wi-Fi

Old Rag Cottage - sunny 2 bedroom near everything

Cheerful two-bedroom riverfront Cottage with Wifi just 1 mi from the Old Rag Trailhead. Brand new spacious kitchen with a charming gas fireplace, deck with wonderful views, and a spacious screened in dining porch. 8 ac of private space on the Hughes River. Terrific fly fishing. Tasteful art decorated space. Spend your days hiking Old Rag and SNP and your evenings in our cozy, elegant Cottage. 15 min from Sperryville's restaurants and amenities. Perfect for a romantic, tranquil getaway from DC.

Location · Family · Quiet

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 no more than one dog, with prior permission. In April 2023, we again upgraded our internet (see below).

Location · Family · Decor

Robinson River Roost - Cottage near Shenandoah NP

Enjoy a slice of country life in our rustic 2 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.

Family · Value · Outdoor spaces

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.

Family · Location · Wi-Fi

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.

Family · Location · Accuracy

Comfy Cottage Near SNP, Hiking, & Wineries

This 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.

Location · Value · Access

Hot tub, sauna, views | Storybook Cottage/cabin

Escape to an absolutely idyllic, Beatrix-Potter–inspired countryside cottage for romance or family time! Surrounded by rolling farmland and stunning Shenandoah mountain views, this modernized retreat offers a truly enchanting getaway in one of the prettiest settings in the Shenandoah Valley. Recently renovated (to the studs), the cottage features a private barrel sauna, hot tub, cozy fire pit, and whimsical, nature-focused décor that blends English-cottage charm with mountain-cabin warmth.

Family · Value · Outdoor spaces

Farm Studio with Blue Ridge views 15 mins from SNP

The Carriage House Studio is perfect for a romantic getaway or quiet escape. Enjoy stunning mountain views from the deck. Hike our private trails. Fish in pond or South River. Enjoy pool. Delight in farm animals including our miniature horses. Less than 20 mins from Shenandoah National Park and Appalachian Trail. Located 2 hours southwest of Washington, DC; 1 1/2 hours east of Richmond; and 25 minutes north of Charlottesville, VA. Near wineries; Monticello, Montpelier, Ash Lawn, and UVA.

Family · Location · Shared spaces