Guesthouse holiday rentals in Clarke County

Private in-law suite Data Center workers welcome

Private Room + Bath on Secluded Farmette — Private Entrance, Kitchenette, Non-Contact Stay, Small Farmette Private room and full bathroom on a small, quiet farmette. Private entrance for easy, non-contact check-in. Kitchenette equipped with a microwave and small refrigerator, perfect for light meals. Comfortable, private backyard space for relaxation. Ideal for up to 3 guests. The owner lives on-site but travels frequently, so you may not see them during your stay. Private back yard for pets.

Welcome to a Perfect Night Stay!

Step into my humble abode, where comfort and warmth embrace you like an old friend. Nestled in a serene and quiet neighborhood, this cozy retreat promises an unforgettable experience. My place carries a gentle hum of tranquility and you'll enjoy a home away from home experience, as every detail whispers hospitality. Whether you're here for leisure, work, or simply to escape, your perfect night awaits. Feel free to make yourself at home, and let the magic of this Airbnb rental envelop you.

1800s Cozy Kitchen House

This award winning whimsical 1800s kitchen house that served the main house is walking distance to all town businesses and great for history and art lovers. Located on historic South Church Street, the property backs to Rose Hill Park, The Barns of Rose Hill music/art venue and the town government center/ library. Everything was chosen piece by piece with respect to the structure’s history with the addition of modern conveniences. Original narrow steps may be difficult for some guests.

Bluemont Escape:Walk to Bears Den; Bear Chase Brew

Charming guest house that is part of a larger estate home property. Walk to Bear’s Den and the Appalachian Hiking Trails as well as popular Bear Chase Brewery. Short drive to wineries, breweries, restaurants, and river. Bluemont escape is located in historic Loudoun County and includes a kitchenette and huge bedroom. This apartment sits on five acres with two other units. Enjoy the sunset from Bear’s Den overlook just across the street, grill out, or enjoy fire pit!

Wine and Horse Country Get-a-way

Stay on a beautiful farm just minutes from downtown Middleburg, wineries, Upperville Show Grounds and festive events. This private top-floor garage apartment offers mountain and horse-farm views, a full kitchen, a spacious living room, a master with a king bed + two daybeds, and a second bedroom with two twins. Enjoy peaceful sunsets after a magical holiday day in town.

Little Acorn Cottage

Kick back and relax in this calm, professionally designed space. The Little Acorn Cottage was completely renovated in 2025! Steps from historic Twin Oaks Tavern Winery est. 1892 and the Appalachian Trail!