Family-friendly holiday rentals in Leesburg

Hummingbirds Hideaway Treehouse

Do not book on airbnb and ask for early arrival. experience the magic of being among the treetops at our newly built treehouse. Whether you are seeking a romantic getaway, peaceful retreat, or family fun this slice of heaven will offer you an unforgettable stay. Features large windows for stunning views of the surrounding woods and very detailed woodwork. 2 bedrooms with king beds, open living space with full kitchen and bathroom will be sure to impress. Please message us prior to booking

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 Forge on Sunnyside Farm

Sunnyside Farm offers a luxurious stay in a beautifully restored historic forge. You’ll be greeted by the farm’s delightful hosts, Jimmy and Dean, two friendly Potbelly pigs. Beautiful cows forage right outside your door. The Forge features exposed wooden beams, brick walls, and cozy furnishings. The interior is designed with plush bedding, a fully equipped kitchen, and spacious living reminiscent of yesteryear. Breweries, wineries and famous antique stores nearby offer entertainment.

The Weaver’s Cottage c. 1815

Welcome to The Weaver’s Cottage c. 1815! This unique and peaceful historic property has been lovingly restored to maintain its original period character while providing modern convenience. Located in historic Waterford, VA, a National Historic Landmark, and close to many farmer’s markets, wineries, breweries, distilleries, restaurants, antiquing, endless outdoor activities, and more, you won’t lack for fun local things to do! The history of the village itself deserves to be explored.

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.

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.

King Bed 3 Bedroom New House

New modern farmhouse in a private, wooded, but centrally located area where the entire family or several couples can escape for an enjoyable weekend near the acclaimed Virginia Wine Country. Paved parking and super fast WiFi. Minutes from some of the best local Vineyards, Wineries and Breweries. Twenty minutes from downtown Leesburg, historic Middleburg, all less than an hour from Washington DC.