
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.

Rustic Blue Ridge Cabins
Quaint Rustic Cabin nested at the top of the Blue Ridge Mountains w/detached 150 ft² bedroom Cabin, located in the heart of Western Loudoun Wine Country. Sitting on 1/3rd acre with access to wooded a trail leads to 5 small cold springs. Amenities 4 person 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! These are rustic not luxurious Cabins
4.99 out of 5 average rating, 641 reviews
The Hunt Box @ Tally Yo Farm
Residence above 5-stall horse barn. Two bedroom house with 2 bath, Juliette balcony, vaulted ceilings, fully appointed kitchen, laundry. Traditional English equestrian decor, with horse shows & fox hunts close by. 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. On site also~AirBnb: www.airbnb.com/rooms/826639006057875355?guests=1&adults=1&s=67&unique_share_id=4cdf4b76-3173-498a-9287-5ab54a38b4ee
4.98 out of 5 average rating, 243 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😊
4.97 out of 5 average rating, 105 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!
4.95 out of 5 average rating, 427 reviews
Farm Stay in a luxury tiny home with hot tub
Welcome to “Horsefeathers” a tiny home on an historic property where you will be immersed in a farm experience! Although tiny, this house is equipped with all top of the line luxuries to include a personal hot tub, an automatic cappuccino maker, a king nectar mattress-just to name a few. Only minutes to Winchester the location is convenient to restaurants and shopping yet you’ll feel like you have been transported back in time to a working homestead where you can interact with all the animals.
5.0 out of 5 average rating, 172 reviews
The Cottage at Nestled Inn
Nestled into the Blue Ridge mountains, practically walking distance from Bear Chase Brewery, Twin Oaks Tavern Winery & The Applachian Trail, our home offers you poolside views of our garden, hottub views of the stars, backyard views of our free range chickens & front yard views of our two horses as well as onsite massage therapy, cats & dogs. While being tucked away, we are still just 10minutes from Purcellville or Berryville & 30minutes from Leesburg, Middleburg, Winchester or Harper's Ferry.
5.0 out of 5 average rating, 115 reviews
Modern Cabin: Hot Tub, Arcade, FirePit, Pets+Pool
Experience the epitome of luxury in our breathtaking A-frame cabin, nestled amidst the serene woods. This modern retreat offers lavish amenities and a stunning open living space with floor-to-ceiling windows, immersing you in nature's beauty. Indulge in the private hot tub, relax by the fire pit, and unleash your culinary skills in our fully equipped kitchen. The large screened porch provides a tranquil oasis, while nearby hiking trails, golf courses, and a spa offer an unforgettable getaway!
4.95 out of 5 average rating, 192 reviews
Have it All, Heated Pool, Hot Tub & Secluded Lake!
Vacloudia-com presents: The ultimate place to unwind and relax — a remodeled farmhouse on four acres with a secluded lake, pool, hot tub, private gym, sauna, and massage chair. With space for up to six guests and six comfortable beds, enjoy this peaceful escape with family and friends. Cook, swim, lounge, fish, unwind in the sauna or massage chair, gather by the lake fire pit, enjoy game or movie nights, explore historic towns, visit Shenandoah National Park, and discover nearby attractions!
4.94 out of 5 average rating, 103 reviews
Unique OASIS - Silo Barn - Swim Pond- 5 Miles Trai
4 unique rentals available (click our profile)! Unwind at this Central VA Country Paradise! Stay in a converted Barn & Silo w/ private natural swim pond and waterfall tucked into the woods on 140 Acres! Your own Oasis awaits, step out on your porch for coffee/drinks with the farm animals. Take a hike around the Lake on the 5+ miles of trails before cooling off in the pond while you gaze up at the stars. Sheep, Dwarf Fainting goats(next to silo 10' away), Chickens, Ducks, Bunnies, & Turkeys.
4.99 out of 5 average rating, 148 reviews
Cottage on Horse Farm: Wineries/Breweries, Horses!
**Pool open May 1- Sept 29 ** 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.
4.95 out of 5 average rating, 290 reviews
Cedar Creek Wayside Castle
1930 Stone House 'Mini Castle' on 9 private acres near Strasburg Virginia bordering Cedar Creek Battlefield and Belle Grove Plantation National Park. Home was built by Otis Elevator company in 1930 for their daughter. You have nature trails and fire pit, swimming pool (opened April 15th), deer and wildlife too. Short walk to historic Ceder Creek. Full estate is yours to play and relax. No dogs in pool. Pool is open early April to early October usually. Hot tub is ready year round.
4.77 out of 5 average rating, 307 reviews
Cozy Secluded A-Frame Cabin Retreat
Visit us on IG @almostheavenwvcabin for the latest photos and cabin moments! Welcome to Almost Heaven Cabin, our beloved A-frame escape tucked away on a private, wooded acre in the heart of the Sleepy Creek Wildlife Management area. Surrounded by 23,000 acres of protected wilderness, this cabin was created as a peaceful family retreat from city life-yet it's just a scenic 1.5-hour drive from DC and Baltimore. Expect quiet mornings, fresh mountain air, and a true West Virginia getaway.
4.99 out of 5 average rating, 139 reviewsPopular amenities for Shenandoah River rentals with a pool
House rentals with a pool

One Of A Kind Home in VA Wine Country on 50 acres
4.93 out of 5 average rating, 261 reviews
COZY3500sf Private-10acres Pool-PickleBall-Hot Tub
4.87 out of 5 average rating, 144 reviews
Wizard's Escape | Sleep15+ | 2 Escape Rooms &Pool
4.92 out of 5 average rating, 161 reviews
Clean 5BR w Heated Pool, Spa - Horse, Wine Country
4.94 out of 5 average rating, 147 reviews
Stoney Spring Overlook
4.95 out of 5 average rating, 156 reviews
Secluded Lakefront | Private Pool | Dock | Hot Tub
4.9 out of 5 average rating, 107 reviews
An Escape Bordering National Park land 1 mi to C&O
5.0 out of 5 average rating, 111 reviews
Mountain Retreat-Stunning View/Hot tub
5.0 out of 5 average rating, 157 reviewsCondo rentals with a pool

Remodeled 1BR/1BA Condo: close to DC with pool!
4.83 out of 5 average rating, 169 reviews
Luxury Condo • In the heart of National Harbor
4.91 out of 5 average rating, 201 reviews
Bike,Hike,Relax in Lux! at Bryce Resort
4.85 out of 5 average rating, 114 reviews
Ski and Golf Condo Aspen East Condos Unit 212
4.93 out of 5 average rating, 154 reviews
Massanutten Woodstone 2-BR, 2 Bath
4.84 out of 5 average rating, 147 reviews
Sunset Ridge (#338) | Walk to Ski Bike Eat!
5.0 out of 5 average rating, 3 reviews
Lovely 1-bedroom condo w/ 2 parking spots near DC
4.77 out of 5 average rating, 62 reviews
SlopeSide
4.98 out of 5 average rating, 42 reviewsOther vacation rentals with a pool

THE PERFECT HIKING & WINERY COUNTRY RETREAT
4.95 out of 5 average rating, 516 reviews
Yurt*FARM*horses*goats*woods*STARS*Hotub*Hiking
4.96 out of 5 average rating, 1302 reviews
Ultimate Group Getaway5 Suites•HotTub•Fall Foliage
4.96 out of 5 average rating, 196 reviews
Herb Cottage-Elegant Cabin plus Optional Farm Tour
5.0 out of 5 average rating, 158 reviews
Round 70s cabin-pickleball, golf, gym, pools
4.98 out of 5 average rating, 104 reviews
Bear Pines Retreat ~ Game Room ~ Screened Porch
4.93 out of 5 average rating, 321 reviews
Mtn Top Cabin: (Szn) Pool/Hot Tub, Infrared Sauna
4.98 out of 5 average rating, 101 reviews
Muse Vineyards Farmhouse, w Seasonal Pool!
4.98 out of 5 average rating, 225 reviewsDestinations to explore
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