Holiday houses in Hillsboro

Homestead 1870 in Wine Country

This cozy two-bedroom rustic farmhouse nestled in Virginia’s wine country and part of a working farm where guests can see farm animals. Close to local wineries, breweries, and delicious food. Located near Harper’s Ferry, the Appalachian Trail, and the Potomac River, perfect for hiking, kayaking, and exploring. Adventure parks and scenic trails are nearby, offering plenty of activities. Relax and enjoy farm life, local charm, and the beauty of Virginia's countryside from a well centered location.

Enchanting PET FREE W/Amazing ViewHot Tub Overlook

Enjoy majestic views of the Shenandoah River in our tiny home centrally located just 5 mins from AppalachianTrail, 6 mins from the rivers, 12 mins from Old Town Harpers Ferry. Featuring large patio, outdoor dining area, courtyard, firepit, hammock, outdoor 2 person soaking tub. The outdoor space provides private vistas of Shenandoah, moonlit nights, star gazing, "Mind Blowing" outdoor soaking tub or taking in the beautiful scenery while enjoying a relaxing shower in our all cedar shower room.

'Waterfront' on 1796 Historic Farm

Feel refreshed when you stay in this rustic gem! The Springhouse is nestled in the rolling hills of Northern Virginia’s Wine Country! Originally constructed in the early 1800's, the structure was built over a natural spring that was used for refrigeration. Water from the spring maintains a constant cool temperature throughout the year while also filling a pond. The original stone well, channel and stone flooring are all intact for guests to explore and experience how our ancestors lived.

Tranquil Treehouse

Nestled on a hillside overlooking the tributary to the Potomac this glammed out cottage has everything you need for a romantic getaway. Immersed just outside the tall glass walls is a private deck overlooking a forest. This property is from our Waterford reservations collection you might get lucky and see a couple of bald eagles on your visit. Enjoy indoor or outdoor shower. The treehouse is completely private and equipped with wifi, kitchen, king bed fire pit nearby and more. Book smart

Hope Flower Farm Winery Cottage

Welcome to Hope Flower Farm & Winery! This charming 3-bedroom, 1-bath cottage is the perfect retreat for those seeking a peaceful getaway in the heart of Loudoun County wine country. The cottage features a kitchen, cozy living room, and a screened-in porch perfect for enjoying your morning coffee or an evening glass of wine. The cowboy cauldron is the perfect spot for roasting marshmallows or enjoying a cozy fire. Come experience the beauty and tranquility of Hope Flower Farm & Winery.

Whole House -Seven Elms Farm B&B

Come and enjoy peaceful setting of our 1870 farmhouse situated close to historical Town of Purcellville, great for shopping and enjoying a good meal, W&OD trail is nearby for a walk or a jog. Or you can just sit on either one of the two covered porches with a good book and take in natural open spaces and a view of a serene pond. And of course we are located in heart of Loudoun County's wine country, great spots for picnic and tasting of great selection of wines.

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.

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!

Modern dreamy mountain view oasis in wine country

Right in the heart of Loudoun County's wine, beer and equestrian country. If you are looking for an outdoor getaway with access to the Ap Trail, biking, kayaking, etc., here for the wine and beer or simply for a change of scenery, this is the place for you. Watch the sun go down right from your bed or, "The Meadow" with the Blue Ridge Mountains as your backdrop. Slowly sip coffee or tea from the hammock, it's up to you. Book now!