Vacation rentals with a pool in Shenandoah River

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Shenandoah River

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

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Guest favorite

Apartment in Bluemont

4.95 out of 5 average rating, 281 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.

Jan 26 – 31

R5,504 ZAR per night

Guest favorite

Cottage in Hamilton

4.94 out of 5 average rating, 309 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!

Sep 17 – 24

R4,878 ZAR per night

Guest favorite

Farm stay in Stanardsville

4.96 out of 5 average rating, 513 reviews

GreeneHouse.POOL*HotTub*MTNviews*FarmGOATS*Hiking

The private, adults 18+only, Greene House apartment is located at ground level of the main farmhouse. Views out the kitchen windows and private patio overlook the piedmont valley. Great for couples or a gathering of 4 adult friends. Private hot tub on porch+shared in-ground pool. A ten minute hike gets you into Shenandoah National Park Back Country. 20 min. to Swift Run Gap SNP. Walking trails. No pets. Check out Cair Paravel Farmstead on FB/the web to see all we have to offer. High speed WiFi

Apr 20 – 27

R2,835 ZAR per night

Guest favorite

Guest suite in Rappahannock County

5.0 out of 5 average rating, 151 reviews

Mountaintop Get-Away in Little Washington

This amazing mountaintop getaway (Reality Mountain) is surrounded by Virginia wine country and overlooks the Blue Ridge. With breathtaking views and 50 wooded acres of mountain retreat, this private venue provides the ultimate discretion and superior taste for discerning guests. The dreamy studio apartment with lodge decor features a king-sized bed and an adjacent slate bathroom with double sinks and a walk-in shower. A stone fireplace and an ivy-enclosed porch complete this romantic escape.

Jun 5 – 12

R5,176 ZAR per night

Guest favorite

Home in Harpers Ferry

4.97 out of 5 average rating, 156 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.

Apr 25 – May 2

R15,693 ZAR per night

Guest favorite

Guesthouse in Monrovia

4.95 out of 5 average rating, 110 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:)

Oct 11 – 18

R3,976 ZAR per night

Guest favorite

Cottage in Bluemont

4.95 out of 5 average rating, 202 reviews

The Cottage @ Red Gate Farm- Horse & Wine Country!

**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.

Sep 27 – Oct 4

R4,189 ZAR per night

Guest favorite

Guesthouse in Troy

4.99 out of 5 average rating, 119 reviews

Beaver Pond Farm - Near Charlottesville

Relax at this unique and tranquil getaway. Sit on the screened in porch and enjoy the sights and sounds of nature while you enjoy a beverage. Take a walk on miles of trails that are adjacent to the property. Visit the Downtown Mall, Monticello, a Winery, a Brewery, or UVA (20 min). Enjoy a dip in the pool (JUN-AUG) or relax by the firepit - perhaps joined by the horses for cocktails. Feel like staying in - SmartTVs and Gig-speed Internet await. Easy checkout. No cleaning fee.

Mar 12 – 19

R2,497 ZAR per night

Guest favorite

Cabin in Delaplane

5.0 out of 5 average rating, 124 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.

Jul 23 – 30

R3,216 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.

Dec 21 – 28

R5,441 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.

R2,193 ZAR per night

Guest favorite

Guesthouse in Highland

4.98 out of 5 average rating, 264 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.

Oct 18 – 25

R2,210 ZAR per night