
Vacation rentals with a pool in Leesburg
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Leesburg
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

A Great Getaway — Foxglove Retreat
Nestled in the Blue Ridge Mountains, "Foxglove Retreat" offers you complete privacy and beautiful vista views of the Shenandoah Valley. Equipped with all the necessities for a relaxed and luxurious experience, the "Foxglove Retreat" is sure to become one of your favorite destinations. "Foxglove Retreat" is ideally located near popular tourist destinations, restaurants and wineries. The Bears Den Trail Center is walking distance for those who would like to explore the beauty of the Blue Ridge Mountains on foot. For those who seek nearby shopping and sightseeing, the quaint village of Middleburg is to the southeast and has many antique shops and elegant boutiques nestled in its historic buildings. To the east is the town of Leesburg featuring the upscale Leesburg Corner Premium Outlets and the Leesburg Farmers’ Market. To the west is the Old Town of Winchester where you will discover charming shops, restaurants, galleries, centuries-old architecture, and historical landmarks.

Nature Zen *Metro Walk *Visit DC *Relaxing Lakes
When you stay here you will experience the comfort of your home and close to various amenities. You can explore nature trails and lakes for a serene retreat. Home is located near Wiehle Reston Metro, providing easy access to D.C and Airports. You will enjoy a fully equipped kitchen with pots, pans, silverware, fridge, microwave, and washer & dryer. Your family will enjoy Gigabit high-speed WIFI for streaming on electronic devices and work quietly from private home office. * Book your stay now! *

*Cottage @ Firefly Cellars* VA Wine Country escape
The Cottage at Firefly Cellars is a private, tranquil escape on the tasting room property. Come enjoy the private pool (in summer months), walk the property with a glass of wine, enjoy views of the neighboring horses, hop to local wineries, or just sit back and enjoy all the cottage has to offer. The cottage is meticulously maintained, beautifully designed, and you will feel at home the moment you walk through the doors. Perfect for a couple, or an individual looking to escape from busy life!

The Hunt Box @ Tally Yo Farm
Residence above 5-stall horse barn. Two bedroom house with 2 bath, Juliette balcony, vaulted ceilings, fully appointed kitchen, laundry. Traditional English equestrian decor, with horse shows & fox hunts close by. Pool open 5/15-10/15. Extra guests $55/night. Pet fee $35 each. Please advise through Airbnb. Lovely antiques, equestrian art & decor, warm rugs. On site also~AirBnb: www.airbnb.com/rooms/826639006057875355?guests=1&adults=1&s=67&unique_share_id=4cdf4b76-3173-498a-9287-5ab54a38b4ee

Chic King 1B Met Park•Costco•Min to DC/Metro/Mall
✨Enjoy a relaxing experience located minutes away from DC, Amazon HQ, and surrounded by popular restaurants and Mall. Our stylish home has a dreamcloud like king-size bed, working space, fast free Wi-Fi, and paid on-site garage parking. With all its amenities along with in-unit laundry for an extended stay, you'll feel right at home, Our home is: ❤ in front of Met park ❤ 2 min walk to Whole Foods ❤ 4 min walk to Metro ❤ 5 min from Reagan National Airport (DCA) ❤ 6 min to National Mall/Museums

Romantic, hot tub, king bed, private, pet-friendly
Uniquely spacious escape for couple, small family, or solo traveler. 30-foot great room, wall of windows facing large deck, oak floors NEW HOT TUB in private setting. King bedroom with en suite bath; loft has twin bed. Modern with touches of mcm & vintage create a magical retreat for you in the treetops. On 2 acres. Hike to top of Cacapon Mountain from back door. Quick drive (3 mins) to private community pool/hot tub/tot pool (summer only). 10 minutes to Berkeley Springs with Roman Baths, arts s

The Cottage at Nestled Inn
Nestled into the Blue Ridge mountains, practically walking distance from Bear Chase Brewery, Twin Oaks Tavern Winery & The Applachian Trail, our home offers you poolside views of our garden, hottub views of the stars, backyard views of our free range chickens & front yard views of our two horses as well as onsite massage therapy, cats & dogs. While being tucked away, we are still just 10minutes from Purcellville or Berryville & 30minutes from Leesburg, Middleburg, Winchester or Harper's Ferry.

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

N. Virginia convenience to DC and Old town Vienna
This is a finished lower level of a townhouse in a quiet Oakton, Virginia suburb of Washington DC. The private entrance side is above ground. The large French doors allow lots of light in. We are located half way between Regan National and Dulles airports with public transportation to both. The bus stop is 50 yards from the door and the bus trip is less than 2 miles to the Vienna/George Mason University Orange line metro station. You will have key to the private entrance and laundry room.

Cottage on Horse Farm: Wineries/Breweries, Horses!
**Pool open May 1- Sept 29 ** PRIVATE 3 hours pool time daily. Plus private patio, grill and fire pit! Horses outside every window! The Cottage is located on a 230 acre horse farm. Red Gate Farm is a full-service, upscale equestrian farm, containing the Cottage, original farm house and 50 horses & ponies. Convenient to Middleburg and Purcellville, you are surrounded by mountains, wineries, breweries, and hiking, with horses right at your doorstep. All in the beautiful town of Bluemont.

Cozy Secluded A-Frame Cabin Retreat
Visit us on IG @almostheavenwvcabin for the latest photos and cabin moments! Welcome to Almost Heaven Cabin, our beloved A-frame escape tucked away on a private, wooded acre in the heart of the Sleepy Creek Wildlife Management area. Surrounded by 23,000 acres of protected wilderness, this cabin was created as a peaceful family retreat from city life-yet it's just a scenic 1.5-hour drive from DC and Baltimore. Expect quiet mornings, fresh mountain air, and a true West Virginia getaway.

Woodland Retreat
Welcome to our private woodland retreat! This stylish and secluded mid-century modern guesthouse is nestled on five acres in horse country in Highland, Maryland. Totally separate from our owners home, our guesthouse combines the serenity, privacy, and safety you crave with all the conveniences of modern life including: a full bath; kitchenette; internet; and a screened porch with access to our beautiful lighted and heated swimming pool (weather permitting) and adjacent walking trails.
Popular amenities for Leesburg rentals with a pool
House rentals with a pool

Stoney Spring Overlook

The Historic Booth House at the Harpers Ferry KOA

4BR: Chef’s Kitchen, Wood Stove, Resort Access

Historic Farmhouse w/ Heated Pool, Harpers Ferry

Wizard's Escape | Sleep15+ | 2 Escape Rooms &Pool

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

Cedar Creek Wayside Castle

An Escape Bordering National Park land 1 mi to C&O
Condo rentals with a pool

Stylish 1BR Condo in Vibrant National Harbor, MD

Wyndham National Harbor ツ 1 Bedroom Deluxe!

Wyndham National Harbor | 1BR/1BA King Bed Suite

National Harbor your D.C. Vacation Springboard.1br

Silver Spring DT LuxePad 2BR, DC Metro, Pool, Gym

Wyndham National Harbor | 1BR/1BA King Bed Suite

DC Views/Walk to Metro jr 1 bedroom

Club Wyndham National Harbor, 2 BR Deluxe
Other vacation rentals with a pool

Driveway Parking, No Stairs, Baby Crib

Mclean Metro, Guest favorite, 1-Bedroom

Long Meadow Cabin Near Wineries & Hiking

Adorable, secluded 2 Bedroom cottage.

Diplomatic stay

Retreat to horse country!

Cozy 1BR1BA Suite with Private Entry Near GMU & DC

Luxury Downtown Crown Apt (Close to DC)
Quick stats about vacation rentals with a pool in Leesburg

Nightly prices starting at
Leesburg vacation rentals start at G$10,458 GYD per night before taxes and fees

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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!
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- Walter E Washington Convention Center
- Georgetown University
- National Mall
- Nationals Park
- The White House
- District Wharf
- Capital One Arena
- Liberty Mountain Resort
- National Museum of Natural History
- Whitetail Resort
- National Museum of African American History and Culture
- Stone Tower Winery
- Arlington National Cemetery
- Washington Monument
- Georgetown Waterfront Park
- National Harbor
- Cunningham Falls State Park
- Smithsonian American Art Museum
- Great Falls Park
- Six Flags America
- The Pentagon
- Lincoln Park
- Library of Congress
- Smithsonian National Air and Space Museum




