Family-friendly holiday rentals in Leesburg

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.

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

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 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 Loft at Lakeside

Welcome to the The loft at Lakeside! The loft is a completely separate space that comes with its own entrance and parking space. The loft consists of a spacious bedroom with a walk-in closet. There is a full bathroom in the bedroom and a half bath near the kitchen. The main space consists of spacious Kitchen that sits right next to the cozy family room, with a large couch. It also has a full laundry room for anyone looking to take home clean clothes after an amazing stay at The Loft.

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.

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!

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!

Quaint Royal Cottage @ Historic Leesburg

Welcome to the Quaint Royal Cottage, a beautifully appointed home nestled in one of Historic Leesburg's most desirable neighborhoods. Just a short stroll away, you'll find an array of dining options ranging from gourmet restaurants to casual eateries, along with numerous brewpubs and vibrant nightlife spots. After a night out, retreat to the serene backyard oasis and relax by the fire pit. Your delightful stay is guaranteed!

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!

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.

Downtown 1 BR Condo Steps to Everything

Large private hideaway, tucked one block from the bustle of King Street. This renovated 2nd floor condo with vaulted ceilings is accessed by a separate secure entrance. Full kitchen includes a 2 top table, toaster, pots & pans, dinnerware, basic cooks tools & coffee maker. Queen size bed with luxury linens & private balcony. 1 full bath. W/D in unit. High Speed Internet. 1 Reserved off street parking space.