Vacation rentals with a pool in Ashburn

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Ashburn

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

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Guest favorite

Cottage in Hamilton

4.94 out of 5 average rating, 308 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!

Dec 2 – 9

R5,063 ZAR per night

Guest favorite

Apartment in Madison

4.9 out of 5 average rating, 229 reviews

The Studio at Dark Run Retreat

Quiet studio on a secluded 5 acres only 3 miles from town. Kick back and relax by the pool in the warmer months, or in the hot tub in the cooler months. Small trails lead to the creek running along the property, maybe you'll even catch a glimpse of the deer or turkey that wander thru...we've even seen a lil bear once! There is an apartment above the studio, so we ask that you be mindful of those guests if occupied. *The studio got a make-over! As of 10/6/20, we will no longer be hosting pets*

Sep 24 – Oct 1

R1,584 ZAR per night

Superhost

Guest suite in Oakton

4.83 out of 5 average rating, 105 reviews

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.

Jun 11 – 18

R1,484 ZAR per night

Guest favorite

Guest suite in Myersville

4.93 out of 5 average rating, 279 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!

Mar 23 – 30

R3,672 ZAR per night

Guest favorite

Home in Harpers Ferry

4.97 out of 5 average rating, 154 reviews

Harpers Ferry Farmhouse, Heated Year Round Pool

Located on the Blue Ridge Mountains of West Virginia, this 1800s farmhouse plus bonus barn studio apartment have been renovated with every modern comfort. The incredible saltwater plunge pool is heated and can be used all year! Perfect for groups. Minutes from outdoor activities, wineries, breweries, and more that make Harpers Ferry, WV such a draw. 1 hour from Baltimore & DC, 3 hours from Philadelphia, 4 hours from NYC. Follow @perennialstays for more details and behind the scenes.

Mar 9 – 16

R14,783 ZAR per night

Guest favorite

Guest suite in Catonsville

4.94 out of 5 average rating, 470 reviews

Rollingside: Two-Room Guest Suite

Two-room guest suite with private entrance located in picturesque Catonsville, MD on a pre-Colonial road originally used for rolling tobacco to the harbor. Downtown Baltimore is 20 minutes away, BWI airport and Amtrak station 15 minutes, and our street is located on a bus route. Beautiful 3.5 mile walk to historic Ellicott City and an hour from Washington, D.C. Individuals and families with children are welcome, but the Airbnb member renting the property must be over the age of 25.

Oct 10 – 17

R1,860 ZAR per night

Guest favorite

Home in Robertson

4.92 out of 5 average rating, 182 reviews

One Of A Kind Home in VA Wine Country on 50 acres

Welcome to Lumusa Lodge. Leave your cares behind as you turn onto the windy road that leads you to this beautiful 50-acre retreat. We are proud to share our home and hope your time here is rejuvenating. Designed/built by a Hollywood actor and situated in wine country, this home is an hour from Dulles, 45 minutes from Charlottesville & 15 minutes from Culpeper. We have an adjacent farmhouse if you need additional space. Great venue for weddings, bachelorettes, and other special events.

Mar 13 – 20

R12,874 ZAR per night

Guest favorite

Farm stay in Purcellville

4.98 out of 5 average rating, 127 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, GORGEOUS 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. Extra guests $55/night. Pet fee $35 each. Please advise through Airbnb. Lovely antiques, equestrian art & decor, warm rugs and fabulous views of Mosby Crossing.

Sep 26 – Oct 3

R5,648 ZAR per night

Guest favorite

Cabin in Delaplane

5.0 out of 5 average rating, 123 reviews

Herb Cottage-Elegant Cabin on Farm plus 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.

Aug 12 – 19

R3,338 ZAR per night

Guest favorite

Home in New Market

4.94 out of 5 average rating, 115 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.

Oct 19 – 26

R5,157 ZAR per night

Guest favorite

Guest suite in Round Hill

4.94 out of 5 average rating, 114 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.

May 24 – 31

R2,640 ZAR per night

Guest favorite

Guesthouse in Highland

4.98 out of 5 average rating, 263 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 and adjacent walking trails.

Sep 18 – 25

R2,296 ZAR per night