Family-friendly holiday rentals in Leesburg

Romantic Secluded Treehouse Stay in the Sky

Your cell# must match acct! Enjoy sounds of nature and view from our amazing treehouse nestled in the Poplar Trees surrounded by woods. Climb steep spiral staircase to a comfortable modern living area with kitchenette and another spiral staircase to a lovely bedroom with king size bed, bathroom and shower. Enjoy your morning coffee on side deck. During winter months you can see Sugarloaf Mountain in the distance. (Make sure to read the other details to note)booking a treehouse in a tree

Leesburg Hideaway w/ King Bed + Private Backyard

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

Rustic Blue Ridge Cabins

Quaint Rustic Cabin nested at the top of the Blue Ridge Mountains w/detached 150 ft² bedroom Cabin, located in the heart of Western Loudoun Wine Country. Sitting on 1/3rd of an Acre with access to wooded a trail featuring Cold Springs. Amenities-4 person hot tub, beautiful view of the Loudoun Valley, Wifi, Loft bedroom with a loft ladder, hiking along the Appalachian Trail,Shenandoah River, with restaurants, breweries, distilleries, and wineries close by! These are rustic not luxurious Cabins

Romantic Barn Loft near Downtown Leesburg!

How about a Fall/Winter Escape to the Country? Welcome to Windy Hill Loft! This is a completely unique stay experience in the Loft built inside our Big Red Barn! Imagine relaxing in this charming space all while overlooking our horses, our adorable mini cows AND the mountains in the heart of Virginia Wine Country. Within 2 miles of some of the best wineries in the area and only a 15 min. drive into downtown Leesburg, Windy Hill is the perfect place to relax after a fun day in the Country!

Big Basement in Bristow, VA

Spacious private basement just minutes from Jiffy Lube Live, 30 miles from D.C., and an hour from Shenandoah. Nearby, enjoy movie theaters and great restaurants. The basement features a private entrance, cozy bed, couches, a private bathroom, a kitchenette with a microwave and fridge (no kitchen sink, stove, or oven), plus a game/exercise area. Whether you're unwinding after a concert, watching TV, playing games, or working out, this space offers comfort and convenience for a relaxing stay.

The Barn at Belgrove

The Barn 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 is located above the barn. It 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 in a rustic environment. There is generally very good cell service but there is no Wifi.

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!

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!

Tranquil Sugarland Retreat Close to Airport/Metro

We welcome you to join us and relax in your own private Sugarland guest suite only minutes to the Metro, Dulles Airport, Reston and Ashburn. Enjoy coffee or tea while sitting on a swinging daybed on your private deck surrounded by nature, and then end the night with a peaceful slumber on a luxurious and comfortable King Size bed. Easy off-street parking for one car provided, with ample nearby street parking.