Holiday rentals with a pool in Loudoun County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Loudoun County

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Flat in Bluemont

4.95 out of 5 average rating, 298 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 favourite

Cottage in Hamilton

4.95 out of 5 average rating, 372 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 favourite

Barn in Delaplane

4.93 out of 5 average rating, 58 reviews

Serene Hideaway w/ Pool: Mim's Barn - Max 4 Adults

Escape from it all! Private, custom-designed retreat at end of dead end road. One of a kind home surrounded by nature, an aging tennis court, salt water pool (seasonal) + built-in spa (year round). Air tight - warm & cozy in winter! Inviting main level with eat-in kitchen and garden views. Queen murphy bed and tiled bath with safety handles allows for one-floor living, if desired. Loft features a king bed, day bed with trundle and desk. No parties or loud noise outside. See below for pool use.

Guest favourite

Home in Lovettsville

4.83 out of 5 average rating, 107 reviews

Cozy 3500sf Private 10ac. pickleball-hot tub-pool

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+

Top guest favourite

Home in Marshall

4.93 out of 5 average rating, 92 reviews

Clean 5BR w Heated Pool/Spa - Horse & Wine Country

Escape the city to this spacious 5BR / 3.5BA home with a heated pool and spa on 8 acres in the heart of Northern Virginia's Horse and Wine country. The house is professionally designed for large groups of adults and kids for family vacations, reunions, and retreats. 2 miles from the one-stop-light town of Marshall with nationally recognized restaurants, bakeries. And in the heart of Virginia's Horse & Wine country - 7 wineries, equestrian facilities/shows, and state park within 15 minutes.

Guest favourite

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.

Guest favourite

Cottage in Bluemont

4.95 out of 5 average rating, 240 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.

Superhost

Home in Reston

4.85 out of 5 average rating, 13 reviews

Serene Lakeside Escape

Forget your worries in this spacious and serene space. Our lakeside home provides you with an amazing variety of amenities including an indoor pool, sauna, poker table, and an outdoor terrace space of over 1,700 SF perfect for outdoor bbqs or just downtime. We’re only a 2 minute walk from Lake Thoreau, which is a serene and beautiful lake that offers fishing, boating, and other water activities. We also have a large open kitchen and a ton of available parking. STL-2024-00066

Guest favourite

Home in Harpers Ferry

5 out of 5 average rating, 20 reviews

*NEW* Riverview Rtrt Pool/HotTub/FirePit & View

Welcome to Riverview Retreat in Harpers Ferry, WV! Come and enjoy our 3bd/2ba home with a hot tub and large pool perfectly situated to soak in the 100-mile views over the Shenandoah River! Centrally located within 15 mins from historic Harpers Ferry; within 1/2 mile of public boat access to the Shenandoah River; 2 miles to Appalachian Trail; less than 15mins to numerous breweries & wineries; 10mins to Hollywood Charles Town Casino. Enjoy all this wonderful area has to offer!

Guest favourite

Guest suite in Purcellville

4.82 out of 5 average rating, 227 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 favourite

Home in Harpers Ferry

4.88 out of 5 average rating, 202 reviews

The Historic Booth House at the Harpers Ferry KOA

The Historic Booth House is great for families for weekend trips or holidays. The house is in a very small neighborhood, located next door the Harpers Ferry KOA Holiday, all of the KOA amenities are included with the your stay (some are seasonal). Each bedroom and bathroom is furnished with linens/towels and basic amenities. Please note this is not a "party" house. No more than 12 people are permitted, day or night. Quiet hours begin at 10pm and are strictly enforced.

Top guest favourite

Farm stay in Purcellville

4.98 out of 5 average rating, 172 reviews

The Hunt Box @ Tally Yo Farm

This is a residence above a 5-stall horse barn. A two bedroom house with 2 bath, Juliette balcony, great views, vaulted ceilings, fully appointed kitchen, laundry, 6 acre farm. Beautifully decorated in traditional English equestrian decor, with homage to the Northern Virginia hunts located just a stone's throw away. 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.