Guest house holiday rentals in Loudoun County

A Hidden Jewel in Loudoun County, Virginia

This charming 5000 sqft huge single family guest house is located just off of Route 7 in the historic town of Hamilton, VA. Enjoy a cup of coffee on the back deck while relaxing in a country environment. Take a walk in a beautiful rural area with magnificent view over the countryside or Enjoy a bike ride on the former W&OD Railroad, which is sitting just outside the house. Listing is for the two upper floors. Access between the basement and the upper floors is locked and secured at all times.

18th Century Middleburg Cottage

This recently renovated 2-story 18th Century stone cottage is the perfect blend of rustic and luxury, featuring stone walls, exposed beams, wood floors, a stone patio and outdoor fireplace, as well as Mountain views. Property includes kitchen, bathroom, and a living space with wood stove and dining table. Upper floor features bedroom and additional reading room. Cottage is just minutes from historic Middleburg in the heart of horse and wine country, perfect for relaxing or recharging getaways.

Modern Sugarland Apt-Metro/IAD

Welcome to our stylish basement apartment, perfect for modern travelers. Whether you're here for work or leisure, this space has you covered. Situated minutes from the Metro, Airport, and major work centers. The apartment features a desk with dual monitors, keyboard, mouse, and 1GB internet. At night, relax in the plush king-size bed. A convertible futon couch with a 65-inch TV, awaits your binge-watching sessions. A washer/dryer and full kitchen, w/refrigerator and stove complete the space.

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.

Private 2 King BR, 1 BA Apartment Near Wineries!

Fox Farm Apartment is a private country retreat, located on 10 acres, on a quiet, private road. It has 2 king bedrooms, one bath, with incredible views (the sunsets are amazing) and filled with natural light. It has a private entrance w/ staircase to 2nd floor. The bath has a luxury shower and dual vanities. It has a full kitchen stocked with cookware, Direct TV, and large family room. Very close to Leesburg and local wineries and breweries. Linens and towels, soaps, shampoos are included.

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.

Fox Hill Barn Guest Cottage Retreat

Enjoy the lovely setting of this romantic spot in nature, just minutes from the historic charm of Middleburg. Set on a tranquil horse property, this cottage offers a serene retreat amidst rolling pastures and breathtaking views. Whether you're a nature enthusiast, equestrian, remote worker, or seeking a romantic getaway, this is your ideal destination. Enjoy nearby wineries, breweries, scenic trails, and the delightful town of Middleburg—only 3 minutes away. Life is too short. Enjoy!

Barn Apartment in VA Wine Country

Barn apartment in the upper level of a bank barn. Fourteen miles from downtown Leesburg, 5 miles from Harper's Ferry, 1 mile from VA-9 Appalachian trail head. Close to Harper's Ferry Adventure Center, wineries, breweries, tubing, kayaking, hiking, farms. Full kitchen. Unplugged with the exception of Wi-Fi - no satellite or TV. There is cell signal. Rate includes 6% Virginia state tax and 7% Loudoun County hotel tax. 1 queen bed, 1 twin, and 1 floor mattress (pull out futon).

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!

A lovely cottage in The Plains, Virginia

The Cottage in The Plains recently underwent a full renovation. It is short walk to restaurants and shops in The Plains and a short driving distance to many attractions (e.g., vineyards, Middleburg, Upperville, and Gold Cup). This one bedroom, 1 bath cottage with full kitchen, living & dining area, work space, and washer and dryer has everything you need for a fabulous weekend getaway or extended stay.