Holiday rentals with a pool in Shenandoah Valley

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Top-rated rentals with a pool in Shenandoah Valley

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

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Top guest favourite
Flat in Bluemont
4.95 out of 5 average rating, 318 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.

Top guest favourite
A tranquil pool area is surrounded by lush greenery and vibrant flowers. The charming cottage, featuring a welcoming porch, is visible in the background under a bright blue sky. The clear water of the pool reflects the sunlight, inviting relaxation.
Cottage in Hamilton
4.95 out of 5 average rating, 410 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!

Top guest favourite
A horse stands peacefully in a lush green pasture, surrounded by a black wooden fence. In the background, a well-maintained barn with a cupola is visible, complemented by a clear blue sky and scattered clouds.
Farm stay in Purcellville
4.98 out of 5 average rating, 212 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

Top guest favourite
A gravel area features several rustic wooden chairs arranged around a stone fire pit, with a gentle fire burning. Soft string lights illuminate the space, enhancing the cozy atmosphere. The exterior of the cabin is visible in the background, surrounded by trees.
Cabin in Hedgesville
4.95 out of 5 average rating, 168 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!

Top guest favourite
Cabin in Dayton
4.99 out of 5 average rating, 206 reviews

Luxurious Cabin By the Creek! Inground pool! Spa!

Rest&Relax with the whole family at this peaceful place to stay while sitting beside the stream. Recently Renovated! Close to many hiking and mountain biking trails. If you love nature, or enjoy time by the water there are many lakes near by. 25 minutes from Harrisonburg and JMU. Close to natural chimney campground. 20 minutes from the West Virginia line. Also has a covered deck with a outdoor bar and a TV. Hot tub conveniently located right off from the bar and deck. Pool open Mar.13-Sep.30!

Guest favourite
The primary bedroom is outfitted with a spacious bed, accented by a blue and white patterned blanket. Two windows allow natural light to fill the room, while dark curtains provide privacy. A dresser and lamp are positioned nearby, completing the relaxing atmosphere.
Farm stay in Stanardsville
4.93 out of 5 average rating, 641 reviews

Tumnus Cabin *pvt HOT tub *SNP*Trails*Pool.

Soak in a private spa, lounge in the spacious screened in porch, take a walk in the woods, enjoy nature & a bit of Appalachia at Tumnus. 10 minute hike to Shenandoah National Park Back Country. Full kitchen. Explore our 58 acres on our private trails. It's easy to visit historical sites such as Monticello or Caverns. Enjoy the Bullfrog hot tub or the seasonal* pool (* Memorial Day-Labor Day) outdoor. Private & self contained. Click on "See more" or visit Cair Paravel Farmstead for more.

Top guest favourite
The living area features large two-story windows that offer views of the surrounding wooded landscape. A cozy leather sofa and armchair are complemented by a wooden dining table with seating for six. Warm lighting and natural textures enhance the inviting atmosphere.
Cabin in Hedgesville
5 out of 5 average rating, 116 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.

Top guest favourite
A panoramic view of rolling mountains is framed by lush green treetops. Soft mist blankets the valleys below, gently illuminated by the sunlight above. The vibrant sky showcases clear blue hues with wisps of clouds, creating a serene and peaceful atmosphere.
Home in Wintergreen Resort
4.97 out of 5 average rating, 118 reviews

Cliffs Edge -A Contemporary Mountain Home

An open floor plan with high ceilings and large skylights, this amazingly engineered home will stun you with its incredible mountain views! This spacious home, with its cantilevered decks, makes this perfect for any family. The large upstairs loft, adjacent to the upstairs bedrooms, offers movies, games, puzzles, and comfortable seating. Wi-Fi, Netflix, and Samsung Smart hub give plenty of entertainment options. The spacious living area and dining room have abundant seating for all.

Top guest favourite
Cabin in Luray
4.92 out of 5 average rating, 219 reviews

Cozy Log Cabin With River and Mountain Views

Only 90 miles from Washington, D.C. Just 5 miles from Downtown Luray, Luray Caverns, and local conveniences. Only 13 miles from the Thornton Gap entrance to Shenandoah National Park. Enjoy breathtaking mountain and river views right from the deck and screened in porch. Listen to the sound of the river which soothes the soul and nourishes the spirit. We do allow well behaved dogs for an additional $50 fee per stay. Limit of two. Sorry no cats, penalty is $200.

Top guest favourite
Double doors framed by potted plants and embellished with decorative wreaths welcome guests into the home. The brick exterior and pathway provide a warm entryway, hinting at the charm within.
Guest suite in Penn Laird
5 out of 5 average rating, 158 reviews

On Cottonwood Pond

A beautiful country setting just minutes from Harrisonburg and JMU, winter snow sports (skiing/tubing/ice skating) at Massanutten Resort, Shenandoah National Park, hiking, other local universities and countless Shenandoah Valley attractions! You won't want to miss the new features in this home with a full kitchen, updated fixtures, plush accommodations and thoughtful touches throughout. Enjoy a quaint getaway in this meticulously designed home away from home!

Guest favourite
A cascading waterfall is observed flowing over rocks and creating a series of smaller falls. Surrounding trees provide a natural setting, with clear water collecting in a serene pool at the base. The sky is partly cloudy, enhancing the tranquil atmosphere.
Cottage in Covington
4.94 out of 5 average rating, 276 reviews

Beaverdam Falls, Earlehurst Cottage

Built for $500.00 dollars "back-in-the-day," the Earlehurst Cottage was inhabited by The Carters, a humble, cute old country couple. Here, they raised two daughters. Today, the house is tastefully appointed where expected - & comfortable to modern standards - yet, it has been left as charming, rustic & cozy as it had always been: with elements of the original decor, windows, plaster walls, etc., being preserved. Pets stay for free!

Top guest favourite
A log cabin is nestled among the trees, featuring a fenced inground pool in the foreground. The pool area is surrounded by a textured patio, complemented by several wooden chairs positioned nearby. The cabin is situated on a gravel driveway, highlighting its private setting.
Cabin in Fort Valley
4.98 out of 5 average rating, 120 reviews

Hidden in Shenandoah Valley|Pool|Pets|Fire Pit

Hidden in the Valley sits on 30 private, wooded acres adjoining the George Washington National Forest. This remote property offers a pool, fire pit and foot trails throughout, perfect for your furry companions! If you’re looking for a true escape to nature, surrounded by Virginia’s best hiking trails, wildlife and clear, starry night skies, Hidden in the Valley is the getaway for you!

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