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

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Guest favourite

Apartment in Bluemont

4.95 out of 5 average rating, 303 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, 381 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

Farm stay in Middleburg

4.95 out of 5 average rating, 65 reviews

Retreat to horse country!

Enjoy your visit while staying in a private country setting complete with a swimming pool and gardens creating a resort like feel. This beautiful family farm includes an English style apartment with large windows, gas fireplace, 1.5 bathrooms, 1 large bedroom with king size bed. An open concept living space, access to the pool a large & outdoor seating and dinning. Minutes to vineyards, Salamander, Goodstone, Upperville and Shadow Creek in Purcellville! Please read “other details” for pet info😊

Superhost

Home in Lovettsville

4.83 out of 5 average rating, 114 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+

Top Guest favourite

Cabin in Bluemont

4.99 out of 5 average rating, 542 reviews

Rustic Blue Ridge Cabin

A quaint rustic cabin nested at the top of the Blue Ridge Mountains, with a detached 150 ft² bedroom, 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- 4person 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!This is a rustic not luxurious cabin!

Guest favourite

Home in Leesburg

4.97 out of 5 average rating, 121 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, 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.

Guest favourite

Guest suite in Purcellville

4.82 out of 5 average rating, 230 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, 206 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.

Guest favourite

Home in Adamstown

4.96 out of 5 average rating, 106 reviews

Wizard's Escape | Sleep15+ | Pool | 2 EscapeRooms

Wizards and Humans are invited to experience the magic of Wizard's Escape. A magical home with an escape room twist. Immerse yourself in this thrilling 2 themed escape rooms. Then, spend hours on our magical scavenger hunt throughout the castle to find the 7 cruxes. Ask about small Weddings or Events and Pool rental are an additional cost. Follow us on Insta or Fb for more videos and pics. Book your favorite Gamekeeper's Hagrid Hut airbnb next door. Link below

Top Guest favourite

Farm stay in Purcellville

4.98 out of 5 average rating, 181 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.

Guest favourite

Farm stay in Hamilton

4.96 out of 5 average rating, 54 reviews

Historic Manor on Beautiful 150 acre Farm

Gorgeous 150 acre equestrian Quaker style farmhouse built in 1856, fully renovated in 2019. Enjoy all the luxurious amenities a on this estate, amongst the most beautiful in Loudoun County. Enjoy the stocked ponds for fishing, swimming pool, outdoor fire pit, breathtaking views, and trails galore. Spend time with our horses, goats, turkey, chicken and peacocks. We are an hour to DC, 10 min to Leesburg and 5 min to Purcellville.

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House rentals with a pool

Home in Lovettsville

4.59 out of 5 average rating, 17 reviews

Dutchmans Creek Farmhouse

HopeRating, 5 stars1 month ago

Wow. What a beautiful location and home with lovely historic charm. We were celebrating my mom’s 60th birthday and she loves history, this was the perfect home to celebrate in. She was so excited and enjoyed every minute. Our weekend didn’t go as planned with the death of my grandfather but the caretaker of the home, Mike, was so kind and understanding with our very late check-in. The communication was awesome and always so warm and kind. Everything about our stay with perfect. Highly recommend!

Guest favourite

Home in Marshall

4.93 out of 5 average rating, 97 reviews

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

KatRating, 5 stars1 week ago

My family was looking for a local weekend getaway, and this house was absolutely perfect! From the moment we arrived, everything felt clean, cozy, and welcoming. Krystal was incredibly responsive and accommodating. We had to do an early check-in due to work call and Krystal made the entire process smooth and stress-free. She was quick to answer any questions we had. The pool was a huge hit with everyone. It was super clean and well-maintained, and we spent most of our weekend swimming, relaxing, and enjoying the beautiful outdoor space. The house itself was fully stocked with everything we needed, from kitchen supplies to extra towels, which made our stay even more comfortable. It was the perfect place to unwind and spend quality time as a family. We had such a great time and made memories we’ll always cherish. Highly recommend this home for anyone looking for a peaceful and fun escape. We would absolutely stay here again!

Superhost

Home in Purcellville

4.88 out of 5 average rating, 25 reviews

Buckskin Manor - Historic, Pool, 66 Acre Vineyard

DeborahRating, 5 stars1 month ago

I would recommend this home greatly. We were on a girls weekend. We enjoyed the home the surroundings and the peacefulness. It’s in a beautiful setting close to many great restaurants and wineries. The beds were comfortable and the homeless clean. Should we ever find ourselves that way again we’ve already decided we would stay here.

Guest favourite

Home in Reston

4.93 out of 5 average rating, 98 reviews

Nature Zen *Metro Walk *Visit DC *Relaxing Lakes

AngelaRating, 5 stars2 weeks ago

This was a very nice place to stay for our family trip to DC. The Metro was a very easy walk and Jagan gave us some great recommendations for local restaurants as well. He was also great at answering our questions.

Guest favourite

Home in Chantilly

5 out of 5 average rating, 11 reviews

Near Airport (IAD) Visit DC | King Bed | WiFi

AmyRating, 5 stars1 month ago

Really lovely home. Well stocked and nice details like luxurious towels and soft sheets. Everything was labeled and well-organized. Very comfortable and great space for a family. Beds were comfortable. Kids loved the huge bathtub!

Home in Bluemont

4.64 out of 5 average rating, 25 reviews

Mountaintop retreat in Bluemont

SamRating, 5 stars1 month ago

We stayed at Fiona's amazing lodge in Bluemont for a night to celebrate my brother's bachelor party and it was the perfect setting. Fiona was very accommodating with check-in and check-out times. Surrounded by beautiful woodlands, the deck is perfect for talking about seeing the sunset. The inside was spotless and exactly like the pictures. All the amenities we needed were provided in the kitchen and bathrooms and made for the perfect environment for the night. We didn't get to do the hike I was thinking about, but the area has some really great trails connected to the Appalachian Trail and some really cool breweries 5 to 20 minutes away. I was a little worried about the TV not being big enough for a shared game night (the one on the bottom floor) but it ended up being a great size for sharing photos and memories. There was a pool that I didn't realize was on the property but it was closed up, would love to come back and try out that sometime!

Top Guest favourite

Home in Harpers Ferry

5 out of 5 average rating, 27 reviews

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

CaitlinRating, 5 stars2 days ago

the stay was wonderful!! we thoroughly enjoyed the pool and hot tub. from photos, the house seemed very secluded but it’s not (no biggie!) it’s also close to nearby towns and the house was well stocked for us. we did lose power due to storms, but Michelle was very responsive and polite. Also, if you have a low riding vehicle beware that you’ll scrape bottom coming out of the driveway. The hot tub was nice, but the accessibility leaves a lot to be desired. the stairs are terrifying lol but once we got the nerve to climb them, it was lovely! the pool was amazing with a lot of provided floats, tubes etc. they also left out their vacuum and skimmers for us to use which was so helpful as a lot of frogs, turtles and bugs got into the pool throughout the night & the storms. overall, we had a great time and i would highly recommend booking. we would absolutely visit again.

Superhost

Home in Reston

4.87 out of 5 average rating, 15 reviews

Serene Lakeside Escape

MaryRating, 5 stars3 weeks ago

This house is fabulous and perfect for large groups. Plenty of space for gathering and privacy if wanted. Hot tub and pool were great. Home recently updated and in great condition. Didn't have time to use the sauna. Neighborhood is quiet, very walkable and beautiful. Easy access to anything you might need or want.

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Holiday rentals with a pool in Loudoun County

Top-rated rentals with a pool in Loudoun County

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