Guesthouse holiday rentals in Loudoun County

The Cottage at Dunthorpe Farm

The Cottage is a restored wagon barn nestled against the Blue Ridge Mountains. You'll enjoy quality, comfort, quietude, and pastoral views. We are a fully licensed and inspected B&B on a 1790's farm in rural Loudoun County VA. Each morning you are treated to a continental breakfast of fresh pastry, fruit sourced from local farms, and homemade jams which we quietly deliver by 7:30 unless otherwise requested. Note that the base price is for 1-2 people. Guests 3 and 4 have additional fees.

Downtown Private Guesthouse - Cozy Bungalow

This Guesthouse is exclusively for Registered Airbnb Guest. Third party bookings are not available. Detached Guesthouse with private entrance. Completely renovated and refreshed for your family. Close to the downtown restaurants and shops, Morven Park, Cornwall Medical Campus, Heritage Hall Health Care Center. A great home base for all Leesburg and Loudoun county have to offer. Our Guesthouse is exclusively offered through Airbnb and is not available as a long-term rental property.

The Cottage

Super private on a farm, newly renovated private 2-bedroom, 2-bathroom guest house surrounded by trees. Updated with new kitchen, baths (full bath on main), freshly painted. Enjoy the serene ambiance on the front porch or gather around the fire pit, stone patio for cozy evenings under the stars, fenced backyard. Abundance of wildlife and birds to enjoy nature and stars. 5 minutes to Rt. 7, 10 minutes to Purcellville, many wineries, venues nearby. Discount for longer stays is firm.

Bright Cozy Guesthouse in Sterling

Forget your worries in this spacious and serene space. Plenty of sunlight and perfect for a weekend gateway. Come enjoy this cozy private guesthouse located adjacent to our house with all the amenities necessary to enjoy your stay. Guesthouse situated on private property with 30 min + drive to exploring wineries, breweries, horse events or civil war sites in Middleburg, Purcellville, Leesburg, Bluemont or Round Hill. Recharge in a peaceful setting.  Adults Only. No pets.

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!

Trailside Chalet (A storybook chalet with hot tub)

The Trailside Chalet is situated on the W and OD Trail, halfway between Leesburg and Purcellville, Va - an ideal base location for visiting wineries, breweries, and the pastoral countryside of Loudoun County. The chalet will put you just steps from the trail for walking/cycling/horseback riding. Relax and enjoy the amenities of one-of-a-kind interior including wood burning fireplace and peaceful surroundings with hot tub. A perfect getaway for a couple or family.

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!

Bear Mountain Cottage

Welcome to Bear Mountain Cottage. This newly built cottage is nestled on a small mountain just under 10 minutes from the edge of downtown Leesburg. Enjoy this beautifully decorated space with all modern amenities. King size bed, open living area, and walk in shower are just a few highlights. Whether you are visiting for a wedding, exploring wine country or in need of a quiet setting, we invite you to enjoy!

Skyhorse Retreat Guest House

In the middle of VA wine country and only minutes to three Appalachian Trail trailheads. Located 45 miles west of Washington D.C., on a 10-acre property on top of the Blue Ridge Mountains. Private guesthouse (built Jan 2020) with a large deck overlooking trees. The Guest House sleeps 4, has a full kitchen, and access to a Hot Tub at the main house. Breakfast items and snacks included.