Holiday rentals in Hogback Mountain

Oatlands Creek cabin

Welcome to Oatlands Creek, the ideal getaway for relaxing & exploring old town Leesburg, Aldie, and Middleburg. This beautifully renovated cabin blends rustic charm with modern comforts, featuring 4 bedrooms; a king-size bed, queen beds, 3 built-in bunk beds & 1 full size bed in the basement. An open dining & living room space, theater room, game room, and hot tub. Whether you're here for a wedding, wine country, family visits, a peaceful retreat, or work, this cabin is the perfect spot for you.

Heart of Loudoun Entire basement!

Guests love it here! Tucked away at the end of the lane yet right in the heart of Loudoun County. Private keyless entrance basement. Natural light filled fully equipped kitchen with full size appliances. King bed (very comfortable per guest reviews), full bath and a very spacious living room with 70" tv or movie screen...you choose! We have super fast Verizon Fios. Not your typical basement. Country living!!! There are many vineyards less than 10 minutes away…happy to make recommendations.

Entire Home in Leesburg – King & Queen Bed +Yard

Escape to this light-filled two bedroom, one bathroom bungalow located minutes from the heart of Leesburg's historic district. Just a short drive from unique shops, restaurants, and outdoor activities. This is the perfect home base whether you're in town for a weekend getaway or an extended stay. Located near the W&OD Bike Trail, Birkby House, Morven Park, breweries, wineries,and Rust Manor. We're excited to host you in our little slice of Leesburg charm! Bikes included: 1 mtn. & 1 cruiser

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.

The Cottage at Forest Hills Farm

Beautiful one bedroom, one bath cottage on a picturesque 14 acre farm just outside of downtown Leesburg. Nestled in close to local vineyards, this charming, free-standing cottage is yours and perfect for a weekend getaway or alternative to a hotel. Enjoy the fresh air, beautiful views, and peace and quiet on our little farm. Wander the property and say hello to our donkey, mule, Long Horn cows, goats, chickens, and 3 barn cats (and 3 kiddos!). Just 3 miles to downtown Leesburg.

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.

Downtown Leesburg Cottage. Walk to everything!

Beautiful cottage in Downtown Leesburg! Walkable to all that Downtown has to offer! Across the street from the iconic Mom's Apple Pie and a short walk to restaurants, shopping, breweries and W&OD trail. Just a short drive to many local wineries, wedding venues, hiking and only 20 minutes from the Dulles Airport. Escape for the weekend or week and enjoy this beautiful 2 bedroom/1 bath home. Equipped with the essentials you need for a more than enjoyable stay!

The Quarters at Belgrove

The Quarters at Belgrove. Welcome to a private and quiet escape on a 67 acre manor in Leesburg. A horse property with abundant wildlife offers a peaceful getaway on an historic property. This full apartment with separate entrance is convenient to downtown Leesburg, Morven Park, and Loudoun's many wineries, breweries and festivals. Most suitable for adults seeking to relax, recharge, and rekindle. There is generally very good cell service but there is no Wifi.

Stunning Views in Spacious Unit

Welcome to our gorgeous apartment in Virginia's wine country! Enjoy a private entrance, kitchenette, and a beautiful master bedroom. Our location puts you just 5 mins away from restaurants, breweries, hiking trails, and downtown Leesburg. Use our 2 available bikes to explore. Stay connected with fast Wi-Fi and unwind on the patio with expansive views. Free parking and nearby Walmart make stocking up easy. Let us make your stay in Leesburg unforgettable!

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!

Steps to Winery and Battlefield | Hot Tub

Unwind at this breathtaking 1-acre hilltop retreat overlooking Antietam Battlefield and lush vineyards. Perfect for a romantic escape or family getaway, our newly remodeled home offers stunning views from the deck, a relaxing year-round hot tub, cozy interiors, and easy access to Antietam Creek Vineyards—just a short walk away! Explore nearby trails or soak under the stars in the hot tub, all while enjoying the comforts of home.