Holiday rentals in Round Hill

Rustic Blue Ridge Cabins

Quaint Rustic Cabin nested at the top of the Blue Ridge Mountains w/detached 150 ft² bedroom Cabin, located in the heart of Western Loudoun Wine Country. Sitting on 1/3rd acre with access to wooded a trail leads to 5 small cold springs. Amenities 4 person hot tub, beautiful view of the Loudoun Valley, Wifi, Loft bedroom with a loft ladder, hiking along the Appalachian Trail, Shenandoah River, with restaurants, breweries, distilleries and wineries close by! These are rustic not luxurious Cabins

Wine Country Loft

Located in the heart of Loudoun Wine Country. Large, peaceful yard in downtown Round Hill, walking distance to a diner and shops. A perfect location for biking, hiking and outdoor enthusiasts. Our friendly dog, Maddie, or cat, Chase, may greet you upon arrival. This studio loft above our carriage house includes one queen bed and a deluxe queen fold out couch.Full kitchen and bath, large projector screen entertainment center, private porch and patio with fire pit.Perfect for families or a couple.

The Cottage at Nestled Inn

Nestled into the Blue Ridge mountains, practically walking distance from Bear Chase Brewery, Twin Oaks Tavern Winery & The Applachian Trail, our home offers you poolside views of our garden, hottub views of the stars, backyard views of our free range chickens & front yard views of our two horses as well as onsite massage therapy, cats & dogs. While being tucked away, we are still just 10minutes from Purcellville or Berryville & 30minutes from Leesburg, Middleburg, Winchester or Harper's Ferry.

Cottage on Horse Farm: Wineries/Breweries, Horses!

**Pool open May 1- Sept 29 ** PRIVATE 3 hours pool time daily. Plus private patio, grill and fire pit! Horses outside every window! The Cottage is located on a 230 acre horse farm. Red Gate Farm is a full-service, upscale equestrian farm, containing the Cottage, original farm house and 50 horses & ponies. Convenient to Middleburg and Purcellville, you are surrounded by mountains, wineries, breweries, and hiking, with horses right at your doorstep. All in the beautiful town of Bluemont.

Cozy Cuddle up on 1700’s Clydesdale Farm

The Hunt Box at Sylvanside Farm is a couples favorite! Cozy bedroom with bay window overlooks the stone barn, Clydesdales field and pond. Full kitchen, full bath and small living room. Enjoy a glass of wine on dock, hike the fields and streams, enjoy the animals, roam the our beautiful 25 acres. Escape the city and relax. Our visitors to date have proclaimed it magical and we hope you agree. In accordance with Airbnb’s policies parties are not permitted.

Farm winery cottage with mountain & vineyard views

Experience the serenity of Good Spirit Farm, a winery, garden, guesthouse & gathering space in Round Hill, VA. Relax in the newly remodeled, fully furnished cottage. Take in beautiful views of mountains, rolling hills and vineyard from the comfortable, open living space and outside decks. Enjoy time spent sipping wine in the winery tasting room or strolling through the expansive grounds. Visit nearby breweries, wineries and the Appalachian Trail.

24 Acre Lamontagne Farm House

Located at the base of the Blue Ridge Mountains in Bluemont, VA only 20 minutes from Leesburg, 5 minutes from Bluemont Vineyards, Dirt Farm Brewing, 10 minutes to B Chord Brewing and Bear Chase, and Henway Cider. This perfect historic house has so much charm and character to offer it makes the perfect getaway for visiting Loudoun County. The other bedrooms are left vacant on purpose and not for occupancy. Please reach out for recommendations : )

Tiny House near Purcellville

Nestled in the heart of Purcellville is a tiny home with a ton of charm. Less than 5 miles from vineyards, LOCO ale trail breweries, cideries, WO&D bike trail & 20 min to historic Leesburg, the Shenandoah river & Appalachian Trail. Our tiny house is a bit larger w/ 2 bedrooms, full kitchen & bath, family room & cozy front porch with private parking. Enjoy a remote work getaway, (our broadband is about 8-10Mbps) relax & enjoy LOCO living!

Starry Night Apt in Va Wine Country

A tranquil setting within the heart of Virginia wine country. Private apartment within a microfarm home located close to many vineyards, distilleries, breweries and hiking/biking trails. Attend a wedding, play croquet on the lawn, or meet your friends to hike the infamous AT 'Roller Coaster' section. Relax at the end of the day and see a million stars like a sparkling carpet in the sky. Welcome! We're so happy for you to visit!

Historic Tip of the Hill, Purcellville, Virginia

Historic Tip of the Hill, ca 1762, is located just a 1/2 mile outside of the town of Purcellville, VA. Close to all the major wedding venues. Restaurants, wine tasting, breweries, live music, the AT, Shenandoah River, W,O&D bike trail & more are just minutes away. This 18th century home has been completely updated but with its charm and character intact. 3 BR, 1.5 BA, sleeps up to 6.

Private Carriage House

A recently renovated carriage house by an interior designer situated on a treed and private property conveniently located for exploring wineries, breweries, horse events or civil war sites in Middleburg, Purcellville, Leesburg, Bluemont or Round HIill. Enjoy the sounds and sights of nature and fresh air. Recharge in a peaceful setting. Adults only. No pets, children or infants.

Snickers Gap Cottage

Historic cottage nestled in the foothills of the Blue Ridge Mountains, minutes from multiple breweries, wineries, hiking and biking trails, and the Shenandoah river. At just 40 miles west of Washington DC it’s the perfect weekend getaway to the country! We are known for our miles and miles of beautiful country roads. Come spend a weekend (or more!) and get lost in Loudoun.