Vacation rentals with a pool in Leesburg

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Top-rated rentals with a pool in Leesburg

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Guest favorite

Apartment in Bluemont

4.95 out of 5 average rating, 300 reviews

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.

Guest favorite

Cottage in Hamilton

4.95 out of 5 average rating, 376 reviews

*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!

Guest favorite

Cabin in Hedgesville

4.94 out of 5 average rating, 116 reviews

Modern Cabin: Hot Tub, Arcade, FirePit, Pets+Pool

Experience the epitome of luxury in our breathtaking A-frame cabin, nestled amidst the serene woods. This modern retreat offers lavish amenities and a stunning open living space with floor-to-ceiling windows, immersing you in nature's beauty. Indulge in the private hot tub, relax by the fire pit, and unleash your culinary skills in our fully equipped kitchen. The large screened porch provides a tranquil oasis, while nearby hiking trails, golf courses, and a spa offer an unforgettable getaway!

Guest favorite

Home in Lovettsville

4.83 out of 5 average rating, 109 reviews

Cozy 3500sf Private 10ac.Pool-hot tub-pickle ball

5/6 (6th bedroom has queen sofa bed) Bedrooms furnished w/linens and all your needs 10 private acres in Farm land views of horses Remodeled fully equipped Kitchen w/new appliances 5 full baths w/spa like showers 7 person hot tub 35,000 gallon in ground private pool opens May 25 Private Tennis Court (basic)/Basketball Court 2 Fire pits Picnic area with grills and patio furniture Kiddos play area w/swing sets and slides Large great room/family room 10 acres with 4 acres a forest Dining for 8+

Guest favorite

Guest suite in Myersville

4.92 out of 5 average rating, 310 reviews

Harmony Lodge nestled in wooded tranquility!

Tranquil lodge nestled on 3 wooded acres in Myersville, MD. Relax by the heated pool, enjoy the warmth of the fire pit, or walk the grounds and enjoy Mother nature. Minutes away from downtown Frederick and Middletown restaurants, shops, and parks. Visit the local wineries and festivals. Tour historic battlefields. Go antiquing. Take in a round of golf, bike the C&O canal, hike the Appalachian trail, boat on the Potomac River, or go skiing. Bring your fur baby with you to enjoy the activities!

Guest favorite

Home in Leesburg

4.97 out of 5 average rating, 120 reviews

Potomac Overlook Farms: 6 BR, 10 Acre River Estate

Welcome to Potomac Overlook Farms, where comfort meets nature on 10 acres along the Potomac River. Surrounded by wineries, breweries, and historic towns, this 5,000 square foot estate offers access to adventure and relaxation. The spacious home comfortably sleeps 16, with an optional guest house for 5. Please inquire about the guest house at booking. Our property, unfortunately, does not offer wheelchair accessibility. The pool is available for your enjoyment from April 1 to October 1.

Top guest favorite

Guesthouse in Monrovia

4.97 out of 5 average rating, 146 reviews

Poolside Paradise in Monrovia, Maryland.

Enjoy your stay in this fabulous pool house located in a quiet neighborhood. Relax poolside during the day and enjoy the outdoor bar and kitchen for cocktails at sunset. Breathtaking views all around. Just 50 minutes from Baltimore and Washington DC and 10 minutes to historic downtown Frederick. Private entrance to backyard with a large green space on the backside of the pool house. We consider ourselves a couples retreat and don’t host gatherings. We look forward to hosting you soon:)

Guest favorite

Cottage in Bluemont

4.95 out of 5 average rating, 244 reviews

Cottage on Horse Farm: Wineries/Breweries, Horses!

**Pool open May1- Sept 14. 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.

Top guest favorite

Guesthouse in Highland

4.98 out of 5 average rating, 288 reviews

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.

Guest favorite

Condo in Centreville

4.91 out of 5 average rating, 104 reviews

Peaceful resort- like patio condo

Stylish 1 bedroom condo on ground level with 1 designated parking space directly in front. This home provides a perfect setting for both luxurious and comfortable living. Bright southern exposure, No steps from parking, 2 smart TV, Highspeed internet, queen size bed, the patio opens to private green nature. Plenty of guest parking as well. Long paved walking trail passing by, Walk to Giant, Starbuck, and Restaurants. Less than 2 miles from Spa World. And 10 min drive to King Spa.

Top guest favorite

Cabin in Delaplane

5 out of 5 average rating, 137 reviews

Herb Cottage-Elegant Cabin plus Optional Farm Tour

Our beautifully restored cabin is the perfect place to relax and enjoy the unique setting of our regenerative conservation farm and the local countryside and vineyards. This elegant cabin offers a charming kitchenette and accessible bathroom while retaining its pre-Civil War character with original wood floors and beams. Curl up in front of the wood stove or enjoy sundowners on the covered deck looking out on our lush pastures or next to the firepit and shared pool and hot tub.

Top guest favorite

Home in New Market

4.93 out of 5 average rating, 138 reviews

Historic Peace and Plenty Farm: Pool House

Peace and Plenty Farm is a 40+ acre, stunning rural escape located in Frederick County, two miles from Historic New Market, 45 minutes from Gettysburg, and an hour from Baltimore or Washington D.C. Feel free to explore our farm’s trails and hidden gems, play yard games with the family, or swim in our lap pool (open from June through October). Our generous space is suitable for a couple's getaway, a weekend with friends, a family vacation, a working vacation, or a quiet retreat.