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Family-friendly vacation rentals in Leesburg

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Leesburg

  • Total vacation rentals

    Explore 40 vacation rentals in Leesburg

  • Nightly prices starting at

    Leesburg vacation rentals start at ﺩ.ﺇ 147 per night before taxes and fees

  • Verified guest reviews

    Over 2,930 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Leesburg vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Leesburg rentals

  • 4.9 Average rating

    Leesburg stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated family-friendly rentals in Leesburg

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite
Villa 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.

Indoor spacesKitchenTV

4.9 out of 5 average rating, 163 reviews
Top guest favorite
The exterior of the cabin is showcased with a green metal roof and rustic wooden siding. Gentle outdoor lighting highlights the structure while lush greenery surrounds the gravel driveway, leading to an inviting entrance. The spacious yard features landscaped gardens and a welcoming atmosphere.
Cabin in Aldie

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.

FamilyKitchenSleep quality

4.99 out of 5 average rating, 152 reviews
Top guest favorite
The backyard features a well-manicured lawn surrounded by a wooden fence for privacy. A large umbrella provides shade over a patio area with outdoor furniture. A storage shed is positioned to one side, and mature trees offer natural greenery.
Home in Leesburg

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

KitchenIndoor spacesCheck-in

4.98 out of 5 average rating, 188 reviews
Top guest favorite
Home in Leesburg

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.

KitchenIndoor spacesView

4.88 out of 5 average rating, 403 reviews
Top guest favorite
A well-lit bedroom features a vintage white metal bed frame with a soft gray blanket and pillows. A wooden dresser and a mirror are positioned beside a rocking chair, while two bedside lamps provide warm illumination. Light flows through the window, flanked by sheer curtains.
Home in Ashburn

Ashburn Manor: 1920’s Farmhouse

Take advantage of this unique opportunity to stay in a beautiful,historic home right in the heart of old Ashburn. Just a quarter mile from the W&OD bike trail, walking distance to several shops/restaurants, 10 min. from Dulles Airport and the metro (easy access to DC), and at the edge of Loudoun County’s vast wine region. The home has been updated with all modern amenities for your comfort. Enjoy BBQ on the patio, books on the sun porch, or coffee on the deck. Peace and serenity await.

FamilyIndoor spacesParking

4.99 out of 5 average rating, 129 reviews
Top guest favorite
Farm stay in Leesburg

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.

KitchenFamilyPets

5.0 out of 5 average rating, 144 reviews
Top guest favorite
The cottage is a charming two-story building, featuring a dark exterior with large windows. A welcoming porch is accented by steps leading to the entrance, and a stone pathway guides through the lush green yard, surrounded by trees.
Cottage in Leesburg

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.

Indoor spacesFamilyBathroom

4.92 out of 5 average rating, 407 reviews
Top guest favorite
The farmhouse is set on a spacious green lawn, surrounded by tall trees. A nearby structure with a cylindrical silo complements the main house, which features a blue-green roof and a wide porch. A bright sky with scattered clouds enhances the serene landscape.
Home in Purcellville

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.

FamilyKitchenTV

4.99 out of 5 average rating, 345 reviews
Top guest favorite
The timber-framed chalet is surrounded by vibrant flower gardens, showcasing various colorful blooms. Large windows and a balcony enhance the exterior, framed by trees creating a natural backdrop. A patio area with seating is visible in the foreground, inviting guests to enjoy the peaceful surroundings.
Guesthouse in Hamilton

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.

KitchenIndoor spacesQuiet

4.96 out of 5 average rating, 183 reviews
Top guest favorite
The open living area features comfortable seating arranged around a circular table. Natural light floods the space through multiple windows, highlighting the light colors of the decor. Wood beams add a subtle architectural element, while a patterned rug anchors the seating area.
Home in 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!

FamilyKitchenComfort

5.0 out of 5 average rating, 213 reviews
Top guest favorite
The exterior of The Quarters at Belgrove is showcased, featuring a charming white facade with decorative paneling. Two large garage doors and a welcoming entrance are visible, complemented by planters filled with vibrant flowers. Natural greenery surrounds the property, enhancing its serene setting.
Apartment in Leesburg

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.

Indoor spacesFamilyNearby

5.0 out of 5 average rating, 225 reviews
Guest favorite
The historical farmhouse is set on a spacious green lawn, surrounded by mature trees. Its brick exterior reflects the sunlight, while the large windows provide a view of the peaceful landscape. The home features a classic gable roof and a welcoming entrance.
Farm stay in Waterford

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.

FamilyKitchenDecor

4.94 out of 5 average rating, 101 reviews

Popular amenities for Leesburg family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favorite
A fenced backyard features a wooden deck with two lounge chairs positioned nearby a circular stone fire pit. Potted plants add greenery to the setting, while string lights hang overhead, creating a relaxed ambiance. A Jacuzzi hot tub is visible in the background.
Home in Leesburg

NEW! Private Home w/HotTub

Indoor spacesKitchenGetting around

4.85 out of 5 average rating, 119 reviews
Top guest favorite
A tranquil pool area is surrounded by lush greenery and vibrant flowers. The charming cottage, featuring a welcoming porch, is visible in the background under a bright blue sky. The clear water of the pool reflects the sunlight, inviting relaxation.
Cottage in Hamilton

*Cottage @ Firefly Cellars* VA Wine Country escape

Indoor spacesKitchenComfort

4.95 out of 5 average rating, 426 reviews
Guest favorite
A spacious outdoor area features a large in-ground pool surrounded by a patio. Lounge chairs in a bright blue color are arranged along the edge. A picnic area with tables and chairs is also visible, along with a children's play area nearby.
Home in Lovettsville

COZY3500sf Private-10acres Pool-PickleBall-Hot Tub

Indoor spacesFamilyHeating

4.87 out of 5 average rating, 142 reviews
Guest favorite
Yurt in Front Royal

Skyline Yurt: Hot Tub~Wood Stove~WiFi~Pet Friendly

Indoor spacesFamilyBreakfast

4.97 out of 5 average rating, 220 reviews
Top guest favorite
The exterior of a large white house is presented, featuring multiple gabled roofs and a welcoming red front door. Large windows allow natural light to fill the interior, while a neatly maintained green lawn enhances the home's curb appeal.
Villa in Haymarket

The Mulberry Manor House

KitchenIndoor spacesAccess

4.99 out of 5 average rating, 101 reviews
Guest favorite
Cabin in Harpers Ferry

Mountain Luxury - Hot Tub, Amazing Views & More!

FamilyIndoor spacesHiking

4.92 out of 5 average rating, 132 reviews
Top guest favorite
An outdoor seating area is set in a grassy space, featuring weathered chairs arranged around a stone fire pit. A wooden picnic table is visible, surrounded by lush greenery and trees. The backdrop reveals a scenic view of the rolling hills under a partly cloudy sky.
Cabin in Bluemont

Rustic Blue Ridge Cabins

KitchenIndoor spacesComfort

4.99 out of 5 average rating, 635 reviews
Guest favorite
The exterior of the farmhouse is showcased at dusk, highlighting the blend of historic and modern architecture. A stone path leads to the welcoming entry, framed by glowing flower pots. The wraparound porch features multiple illuminated windows, reflecting a cozy and inviting ambiance.
Home in Harpers Ferry

Historic Farmhouse | Heated Plunge Pool, Billiards

Indoor spacesKitchenAccess

4.96 out of 5 average rating, 219 reviews

Family- and pet-friendly home rentals

Top guest favorite
Guesthouse in Leesburg

CozyLeesburgCottage-Private Home Downtown Leesburg

KitchenIndoor spacesHospitality

4.96 out of 5 average rating, 583 reviews
Guest favorite
The exterior of a two-story historic home features clapboard siding painted in light blue. A red door stands at the center, flanked by white shutters. An American flag is displayed next to the entrance, while a brick pathway leads to the front steps.
Home in Leesburg

Historic home in the heart of downtown Leesburg!

FamilyKitchenWifi

4.97 out of 5 average rating, 119 reviews
Top guest favorite
A well-appointed living area features a spacious sectional sofa and an adjoining dining space. Large windows allow natural light to illuminate the room, creating a bright atmosphere. The kitchen is visible in the background, featuring high-end appliances and modern design elements.
Home in Sterling

The Villa on Lakeside

FamilyKitchenGetting around

4.97 out of 5 average rating, 143 reviews
Top guest favorite
A modern living area is highlighted by a comfortable sectional sofa adorned with colorful cushions. A round coffee table sits in front, with a decorative item placed on top. Large windows allow natural light to illuminate the space, framed by soft curtains and offering views of greenery outside.
Apartment in Sterling

The Potomac Perch-Peaceful Cozy Family Apt

FamilyIndoor spacesPets

4.99 out of 5 average rating, 128 reviews
Guest favorite
The historic stone house features a grand facade with white columns and a peaked roof. Lush greenery surrounds the property, including a vibrant tree in the foreground. The entryway showcases two symmetrical doors, enhancing the home's classic architectural style.
Farm stay in Hamilton

Historic Farmhouse in Beautiful Western Loudoun

Indoor spacesKitchenAmenities

4.95 out of 5 average rating, 262 reviews
Guest favorite
A bright living area is presented with large windows allowing natural light to fill the space. Comfortable furnishings include a sectional sofa and a circular coffee table, while a patterned area rug adds warmth. A television is mounted on a dark cabinet, enhancing the room's functionality.
Farm stay in Purcellville

50-Acre Farmhouse Getaway Oasis in VA Wine Country

FamilyIndoor spacesValue

4.98 out of 5 average rating, 165 reviews
Top guest favorite
A historic cottage features a log exterior and a distinctive red metal roof. Surrounded by lush greenery and colorful flowers, the property is set back from the road, offering a peaceful rural aesthetic. The front porch provides outdoor space with views of the natural landscape.
Cabin in Waterford

The Weaver’s Cottage c. 1815

KitchenIndoor spacesLocation

4.97 out of 5 average rating, 114 reviews
Top guest favorite
A charming outdoor seating area features red wooden chairs and a fire pit, surrounded by lush greenery and pavers. The Cottage, with its welcoming facade and gray metal roof, is visible in the background, offering a cozy retreat in a natural setting.
Cottage in Bluemont

Cottage on Horse Farm: Wineries/Breweries, Horses!

FamilyIndoor spacesOutdoor spaces

4.95 out of 5 average rating, 288 reviews

Family-friendly home rentals with a pool

Top guest favorite
Guest suite in Herndon

Capital Escape-Unique Spacious 2BR/1BA Apartment

FamilyIndoor spacesHeating

4.95 out of 5 average rating, 102 reviews
Top guest favorite
A well-maintained sign for Tonka Farm is positioned at the entrance along a gravel driveway. Lush green grass surrounds a neatly trimmed shrub. Black wooden fencing lines the pathway, leading to a serene and inviting country setting.
Farm stay in Middleburg

Retreat to horse country!

KitchenIndoor spacesGetting around

4.97 out of 5 average rating, 102 reviews
Top guest favorite
A spacious pool area features a heated in-ground pool and spa surrounded by lounge chairs. A well-maintained lawn and shaded seating areas complement the outdoor space, while a house is visible in the background, nestled among the trees.
Home in Marshall

Clean 5BR w Heated Pool, Spa - Horse, Wine Country

FamilyIndoor spacesPool

4.94 out of 5 average rating, 147 reviews
Guest favorite
Home in New Market

Historic Peace and Plenty Farm: Pool House

FamilyIndoor spacesWalkability

4.92 out of 5 average rating, 163 reviews
Top guest favorite
A spacious backyard is surrounded by a wooden fence, showcasing a patio area with multiple seating options. A hot tub is visible, along with a fire pit and several Adirondack chairs arranged for gathering. Lush green grass and mature trees enhance the outdoor setting.
Home in Harpers Ferry

The Historic Booth House at the Harpers Ferry KOA

KitchenFamilyBathroom

4.89 out of 5 average rating, 235 reviews
Top guest favorite
A clear saltwater pool is surrounded by a wooden fence, with a spacious deck area nearby. The pool's surface reflects the sky, and lush green grass borders the surrounding area. A modern building is visible in the background, set against a cloudy sky.
Guesthouse in Midland

Modern Farm Stay

FamilyIndoor spacesAir conditioning

4.97 out of 5 average rating, 259 reviews
Superhost
A lush backyard is captured during sunset, featuring vibrant greenery and a spacious pool. The scene includes wooden steps leading down to the lawn, complemented by a large umbrella and a gazebo in the distance. Soft orange and purple hues illuminate the sky.
Guest suite in Purcellville

Monet Suite, elegnt lrg 2rm suite/blcny in villa

Indoor spacesKitchenBiking

4.81 out of 5 average rating, 244 reviews
Top guest favorite
A warm interior features a spacious bed dressed in a rich, burgundy coverlet, complemented by wooden wall panels and exposed beams. A cozy seating area is provided next to the bed, with light streaming in from a window adorned with wooden shutters.
Cabin in Delaplane

Herb Cottage-Elegant Cabin plus Optional Farm Tour

FamilyIndoor spacesAccuracy

5.0 out of 5 average rating, 156 reviews

When is the best time to visit Leesburg?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 830ﺩ.ﺇ 735ﺩ.ﺇ 852ﺩ.ﺇ 955ﺩ.ﺇ 1,021ﺩ.ﺇ 1,050ﺩ.ﺇ 735ﺩ.ﺇ 738ﺩ.ﺇ 753ﺩ.ﺇ 782ﺩ.ﺇ 837ﺩ.ﺇ 837
Avg. temp1°C3°C7°C13°C18°C23°C25°C24°C20°C14°C8°C3°C

Destinations to explore