Family-friendly vacation rentals in Leesburg

Luxury Private Estate with 6 Bedrooms in Leesburg

luxury Private Estate in Leesburg. Perfect for family fun near wineries & breweries! with 6Bedrooms, huge owners suite & lux bath w/heated floors, soaking tub. The primary suite has a private living room that leads to a balcony. Huge open kitchen with high-end appliances, double wall-oven, oversized island, granite counters, skylights, heated floors, new sunroom, Bluetooth ceiling speakers. Covered Porch with Brand New Hot Tub. Beautiful outdoors with firepit under the stars. Welcome to Harmony.

Family · Kitchen · Value

Oatlands Creek cabin

Welcome to Oatlands Creek, the ideal getaway for relaxing and exploring Old Town Leesburg, Aldie, and Middleburg. Set on 22 private acres, driving up you’ll be greeted by horses in the neighborhood. This beautifully renovated cabin blends rustic charm with modern comforts, featuring 4 spacious bedrooms, an open dining and living space, theater room, game room, and hot tub. Whether you’re here for wine country, family visits, bachelorette parties, or work, this cabin is the perfect spot for you.

Kitchen · Indoor spaces · Checkout

The Potomac Perch-Peaceful Cozy Family Apt

Step into a calming and contemporary haven. This thoughtfully designed one-bedroom apartment features a spacious bedroom with full bathroom , a modern full kitchen perfect for preparing your favorite meals, and comfortable living areas. The bright and airy layout, with its clean lines and tasteful decor, creates an inviting atmosphere for relaxation after a day of exploring. Nestled in a quiet and peaceful neighborhood along Broad Run Drive, you'll be just moments from the scenic Potomac River.

Indoor spaces · Family · View

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

Kitchen · Family · Amenities

Historic Cottage • Walk to Everything • Parking

Stay on the most storied block in Historic Leesburg. This sparkling-clean, beautifully updated cottage — once the neighborhood candy store — sits two doors from a famous Civil War landmark and steps from downtown's restaurants, wine bars & shops. Enjoy the peaceful side porch, private patio, 2 cozy bedrooms, full kitchen & laundry, and covered parking (rare downtown!). Vintage character, modern comfort. The framed history inside tells the block's wild story — ghosts and all. Welcome home.

Indoor spaces · Family · Parks

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.

Family · Kitchen · Location

Whole House -Seven Elms Farm B&B

Come and enjoy peaceful setting of our 1870 farmhouse situated close to historical Town of Purcellville, great for shopping and enjoying a good meal, W&OD trail is nearby for a walk or a jog. Or you can just sit on either one of the two covered porches with a good book and take in natural open spaces and a view of a serene pond. And of course we are located in heart of Loudoun County's wine country, great spots for picnic and tasting of great selection of wines.

Family · Kitchen · Parking

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.

Family · Indoor spaces · Hot tub

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!

Family · Kitchen · Nearby

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.

Family · Indoor spaces · Nearby

Laurel Hill Historic House & Farm with Hot Tub

Hidden on its own private lane, this 18th century farmhouse gives guests the chance to experience the past. Laurel Hill Farm was originally settled in 1762 with several additions in the following centuries. The house has been restored and updated to include modern amenities. Among the charming period features are hand blown glass windows, exposed brick walls, original wide board pine floors, all of which are blended seamlessly with modern amenities.

Family · Kitchen · Value

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.

Kitchen · Family · Walkability