House holiday rentals in Clarke County

Cottage on the Shenandoah

Situated along the banks of the Shenandoah River and base of the Blue Ridge Mountains--perfect for your escape to nature! Nearby attractions include the Blue Ridge Wildlife Center, Sky Meadows State Park, the State Arboretum, & Appalachian Trail. Whether you're looking for outdoor adventures or a relaxing getaway, you will find it here. Only 20-25 minutes from the historical and walking attractions of Winchester, Front Royal, Middleburg, wineries, breweries, and a five star French restaurant.

Summit Point Historic "1850's House"

Set in Jefferson County, WV, this historic home built in 1850 has been transformed into a modern, bright and serene home away from home. The home is close to Winchester & Berryville, VA, & the historic West Virginia towns of Charles Town, Harpers Ferry and Shepherdstown. Whether you are here for the Summit Point races or the Charles Town Casino, or in town for a tour of our historic towns, hiking or tubing on the C&O and Potomac rivers we know you will have an amazing stay! NO PARTIES ALLOWED

Purple Iris 3b 2b private oasis nr river/mountain

Come get away and relax in this stunningly decorated one level light-filled home on its own private oasis. “Purple Iris” is a magical place with an artistic feel & several modern amenities. Perfect location for visiting local wineries, taking a hike & going to small town shops & restaurants in downtown Berryville. Awesome fully stocked kitchen & outdoor deck with grill! You will LOVE it! Skyline Drive - 20 min Harpers Ferry- 20 min Shenandoah River - 5 min DC - 1.5 hr. Pets are welcome!

The Old Schoolhouse at High Meadows Estate

The Old Schoolhouse at High Meadows is a beautifully appointed historic cottage set amidst a tranquil 15 acre estate of gardens and old barns. Close to wineries, breweries, the Appalachian and W&OD Trails and many historic villages (Middleburg, Upperville, Harpers Ferry) and only minutes from the Shenandoah River, this superbly decorated cottage is a wonderful get away from Washington DC and perfect for a couple or small family. Activities abound, or just visit local farmers’ markets and read.

The Hill House at Stubblefield

Enjoy spectacular views of the Blue Ridge from this meticulously crafted stone house. The Hill House is situated on 40 acres in beautiful Clarke County, Virginia, and offers easy access to any outdoor activity your heart desires. This getaway is 2 miles from a public boat landing, and is surrounded by pastoral views and country roads in all directions. The Hill House is on Stubblefield Farm, which has its origins dating back to 1792. Come enjoy local wineries, breweries, and antique shops.

Beautiful Cottage in the Heart of Wine Country

Located at the crest of the Blueridge section of the Appalachian Mountains across from the Appalachian Trail and Bears Den, experience an incredible stay in the heart of Loudoun County wine country. Half a mile from Bear Chase brewery and minutes from Bluemont Vineyard, Dirt farm and others. If you like music Tally Ho in Leesburg has many great shows. Shopping and restaurants head to the quaint village of Middleburg, 25 minutes away. 50 minutes from Washington, DC. The views are stunning!

Hot tub, prime leaf peeping and more! Gorgeous 4BR

This gorgeous chalet perched on a high hill is surrounded with trees and features an enormous wrap-around deck, HOT TUB, wood-burning fireplace, huge smart TVs and a GAME ROOM for adults and kids with every fun game you can imagine- pool, ping pong, PacMan video arcades, darts and more. Each bed is new and there are king beds and trundle beds to accommodate visitors of all ages. Please note there is an extra charge of $75 for first dog, $25/ea for 2nd/3rd (2nd/3rd dog fees charged later).

Colonial Getaway Near Old Town Historic Winchester

Colonial style home- enjoy a spacious home with large living room, dining room, kitchen, 3 bedrooms and 2.5 bathrooms. Perfect for a family or a longer stay. Just a few miles drive to Old Town Winchester which includes numerous restaurants, bars, shopping and some kind of event... like the Shenandoah Apple Blossom Festival! Our house is located about 65 miles West of Washington D.C. Near by to other scenic attractions as well- Shenandoah National Park, Luray Caverns, and Harper's Ferry!

Deer Chase

Welcome to our renovated cabin, “Deer Chase”, incredibly convenient to Clarke County's Ruritan Fairgrounds, Rosemont Manor, wineries, breweries, Appalachian Trail, and more. This is just off Rte 7, located between Loudoun and Frederick Counties, less than 10 minutes to 81, in a private and relaxing setting. Looking for convenience to local amenities, in town for a wedding, Lucketts Fair, or Apple Blossom Festival, or just passing through and just need to kick your feet up, you found it.

Couples Getaway (maximum of two guests)

Your party of up to two guests are welcome to stay in the beautiful Randolph room. You will have complete and exclusive access to the entire house with the exception of the basement. Enjoy a 10% discount for a two night or longer stay in historic family home. Our home is situated in the middle of our 400 acre working cattle and sheep farm, and near the Shenandoah River, the Blue Ridge Mountains and the Appalachian Trail. We are located less than 45 minutes from Dulles Airport.

Upperville Hunt Country Cottage

The home has a standing seam metal roof, clapboard-style siding, a stone foundation, a cozy front porch, and second-floor dormer windows. The interior is painted with warm colors and accented by antique oak barn wood paneling and trim in the family room. The flooring is the original antique heart pine. The cottage is decorated as a traditional English Hunt Box, with equine art and memorabilia, lovely antiques, warm carpets on the heart pine floors, and high-end bed linens.

The Ladybug Retreat

Welcome to the Ladybug Retreat! Nestled on 18+ wooded acres in Boyce, Virginia, this is the perfect spot for your group’s getaway. Our location offers a balance of seclusion and proximity to activities. We're less than 10 minutes from a state park, the Virginia State Arboretum, and a Shenandoah River boat ramp. Conveniently situated between historic Middleburg and vibrant Winchester, you’ll also have easy access to the area’s best vineyards, dining, and shops.