Vacation rentals with a pool in Loudoun County

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Top-rated rentals with a pool in Loudoun County

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Guest favorite

Rental unit in Bluemont

4.95 out of 5 average rating, 297 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, 348 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

Home in Lovettsville

4.83 out of 5 average rating, 105 reviews

Cozy Hemingway Retreat 3500sfHotTub Pool Tennis Ct

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

Rental unit in Herndon

4.93 out of 5 average rating, 68 reviews

Woodland Park Studio | Yard & walkable to Metro

Wake up in the modern, spacious studio with peaceful forest view located Herndon, VA, bordering Reston. End unit townhouse with a separate entrance, spacious 1 bedroom with a private bath and kitchen. Parking on the community premises. Beautiful fully remodeled kitchen. Among the amenities are two tennis courts, gym, two pools* and more. Perfect 15 minutes walking distance to the Herndon Metro Station. Shopping plaza with supermarket, Sushi and Kabob restaurants, and more are 5 min away.

Guest favorite

Tiny home in Bluemont

5 out of 5 average rating, 28 reviews

The Coop

Welcome to The Coop! Nestled in a wooded mountain community, this rustic hen house has been lovingly transformed to offer a unique off-the-grid experience. Within 2 miles of both the Appalachian Trail & wineries, The Coop blends rural charm with modern comforts through solar-powered amenities, fresh linens, telescope stargazing & a secluded fire pit. While there haven't been hens at The Coop in decades, guests are welcome to enjoy their fresh eggs & visit them living happily across the street!

Guest favorite

Home in Harpers Ferry

4.97 out of 5 average rating, 180 reviews

Harpers Ferry Farmhouse, Heated Year Round Pool

Nestled in the Blue Ridge Mountains of West Virginia, this lovingly restored 1800s farmhouse and barn studio is the perfect blend of historic charm and modern convenience. Relax in our year-round heated saltwater plunge pool. Ideal for groups, the farmhouse is just minutes from hiking trails, vineyards, and breweries. Conveniently located only an hour from Baltimore and DC, and within easy reach of Philadelphia and NYC. Follow @perennialstays for exclusive details and behind-the-scenes.

Guest favorite

Home in Leesburg

4.97 out of 5 average rating, 115 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 May 1 to October 1.

Guest favorite

Cottage in Bluemont

4.95 out of 5 average rating, 230 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.

Guest favorite

Cabin in Harpers Ferry

4.87 out of 5 average rating, 23 reviews

Mountaintop Cabin w/ Poolside Sunsets!

MOUNTAIN MAMA VACATION HOMES Trying to decide between dramatic views and a poolside escape? How about both! The pool at this mountaintop cabin is perfectly situated to soak in the 100-mile views over the Shenandoah Valley. Once you've had enough sun, curl up on one of the man porches for a lazy afternoon, or wind down the day at the rock fire pit. When the weather cools you can warm up indoors at the pellet stove in the epic great room. You are going to love this cabin escape!

Guest favorite

Cottage in Harpers Ferry

4.95 out of 5 average rating, 220 reviews

Harper's Ferry Tree House/ hot tub / nature/ trees

Cozy cabin in a private community minutes away from downtown Harper's Ferry. This cottage in the trees is situated on a private wooded road and has parking for 5 vehicles. You'll enjoy a large deck, inflatable hot tub, outdoor fire pit, and gated access to a beautiful picnic area with canoe/kayak/swim spot on east side of Shenandoah River. If you are interested in fishing/boating/tubing/swimming this spot cannot be beat . Ride the commuter train to DC to take in the sites. Enjoy!

Guest favorite

Guest suite in Purcellville

4.82 out of 5 average rating, 226 reviews

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

"Monet Suite", elegant and well appointed furnished 2 rm spacious private master suite, trey ceiling, king size bed (one couch is a castro convertible), original oil paintings; private balcony. Magnificent mountain views in artist villa located in heart of Loudoun's wine and burgeoning craft beer breweries and Virginia horse country; Roman shower for 2 with spectacular views, as well as Jacuzzi for two with same views. Breakfast room service is available for $30 per person.

Guest favorite

Guest suite in Round Hill

4.93 out of 5 average rating, 129 reviews

Sweet Suite on Snickersville!

Located near the town of Bluemont. The suite is located above a 3 car garage and is detached from the main house with about 450 sq ft. Has a queen bed & a loveseat sleeper sofa, a 3/4 bath, a breakfast nook with refrigerator, microwave & coffee maker. We are within 3 miles of Bear Chase Brewing, Dirt Farm, Bluemont Vineyard, Good Spirit Farm and more! Purcellville is a 15 minute drive has many amenities, major grocery stores, restaurants, golf courses and tennis courts.