Holiday 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 favourite

Flat 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.

2–7 Sep

$413 SGD per night

Guest favourite

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!

17–24 Dec

$367 SGD per night

Guest favourite

Farm stay in Stanardsville

4.96 out of 5 average rating, 511 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

15–22 Feb

$213 SGD per night

Guest favourite

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!

6–13 Dec

$251 SGD per night

Guest favourite

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.

9–16 Mar

$1,019 SGD per night

Guest favourite

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.

13–20 Dec

$315 SGD per night

Guest favourite

Guest house in Troy

4.99 out of 5 average rating, 118 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.

19–26 Sep

$186 SGD per night

Guest favourite

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.

10–17 Nov

$242 SGD per night

Guest favourite

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.

21–28 Sep

$409 SGD per night

Guest favourite

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.

24–31 May

$191 SGD per night

Guest favourite

Guest house 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.

2–9 Oct

$167 SGD per night

Guest favourite

Cabin in Hedgesville

4.93 out of 5 average rating, 134 reviews

Stylish Retreat with Pool Access and Fire Pit

Experience a peaceful getaway at The Woods Resort. With an outdoor screened porch, a fire pit and a wood burning fireplace, you can comfortably enjoy this retreat in any season! With an additional fee you can enjoy access to two outdoor pools, an indoor pool with hot tub, tennis and pickle ball courts, a gym, and 36 holes of golf. Close to the Sleepy Creek WMA, public river access, Berkeley Springs and tons of hiking - enjoy the indoors or outdoors in any season.

26 Jan – 2 Feb

$195 SGD per night