Vacation rentals with a pool in Madison County

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Top-rated rentals with a pool in Madison County

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

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Top guest favorite

An aerial view captures a green two-story home surrounded by lush landscaping, featuring a pool with lounge chairs and a patio area. The backyard includes a hot tub and shaded seating, inviting relaxation. Vibrant spring foliage adds color to the serene outdoor setting.

Home in Madison

5.0 out of 5 average rating, 48 reviews

NEW l Near Shenandoah•Pool•Hot Tub•Fire Pit•10Acre

Welcome to Emerald Retreat! Tucked away on 10 peaceful acres in Virginia's scenic countryside, this is your ultimate escape into nature. Perfect for a family reunion or a friends’ retreat, this spacious 6-bedroom, 4.5-bath home offers a pool, hot tub, fire pit and more. Designed for unforgettable memories. Just minutes from Shenandoah National Park, local wineries, craft breweries, University of Virginia, and Charlottesville - this property offers outdoor adventure and wine-country relaxation.

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Top guest favorite

A private hot tub is positioned on a wooden deck, inviting relaxation. The exterior of a two-story building is visible in the background, featuring a well-maintained lawn and a staircase leading to a covered porch. Soft lighting illuminates the outdoor seating area.

Apartment in Madison

4.91 out of 5 average rating, 277 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*

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Top guest favorite

The entrance to Fairhill Farm is marked by a white wooden sign displaying the name, set against a backdrop of rolling hills adorned with autumn foliage. A vibrant red bush frames the sign, contributing to the natural beauty of the landscape.

Home in Stanardsville

4.98 out of 5 average rating, 174 reviews

Farm Cottage w. Blue Ridge views 15 mins from SNP

Carrie's Cottage is nestled in a private corner of our 150-acre Fairhill Farm. Delight in the bold views of the Blue Ridge Mountains. Hike our private trails. Fish in pond or river. Enjoy pool. Delight in farm animals including our miniature horses. Less than 20 mins from Shenandoah National Park and Appalachian Trail. Located 2 hours southwest of Washington, DC; 1 1/2 hours east of Richmond; and 25 minutes north of Charlottesville, VA. Near wineries; Monticello, Montpelier, Ash Lawn, and UVA.

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Guest favorite

An outdoor patio area features a saltwater heated pool surrounded by lounge chairs and a stylish sectional sofa. A large umbrella provides shade, and manicured greenery and a cabin are visible in the background, creating a serene atmosphere.

Cabin in Etlan

4.85 out of 5 average rating, 13 reviews

Mountain Cabin w/ Pool - Birdwatchers’ Paradise!

Walnut Hill is a mountain cabin nestled on 9 acres adjoining Shenandoah National Park. A peaceful escape from the stresses of everyday life. The property features beautiful mountain views and a saltwater pool (Apr.-Oct). The pool can be heated for $100 during cooler months. The cabin offers 4 bedrooms and 2 baths. Relax on the front porch swings, sit by the outdoor fire-pit or lounge at the pool. Nearby attractions include Old Rag Mtn., White Oak Canyon, Graves Mtn Lodge and Sperryville.

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A dwelling featuring a wooden deck and a second-floor balcony is positioned against a backdrop of rolling mountains and open fields. The sky is painted with soft, muted colors, reflecting a peaceful rural landscape.

Home in Reva

4.69 out of 5 average rating, 26 reviews

"Country Living at It's Finest"

CLOSE TO EVERYTHING BUT AWAY FROM IT ALL!! The Cottage is self-contained with charming porches, centrally located to a multitude of things to do and offers an unequaled experience of the best of country living with all the creature comforts including a pool! Rural setting, gorgeous mountain views, history, hiking, wineries and more. Sleeps , 3 bedrooms, 3 bath,LR, DR, equipped kitchen, linens provided, gas grill and firepit. Pets allowed with prior approval. Since 2006 with Excellent reviews

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Top guest favorite

The exterior of the cottage showcases a well-maintained garden featuring blooming flowers. A scenic view of a tranquil pond is visible, with rolling hills and trees in the background. The sky features scattered clouds, enhancing the serene atmosphere.

Farm stay in Stanardsville

5.0 out of 5 average rating, 14 reviews

Guest Cottage @ South River Farm

Escape to the serenity of South River Farm, nestled in the picturesque Virginia Piedmont. Only 15 min to Shenandoah National Park, our charming studio cottage boasts a luxurious king-sized bed, chic new furnishings, cozy en-suite bathroom, and state-of-the-art appliances, ensuring a relaxing stay. As our guest, revel in the expanse of our working farm: roam miles of bucolic trails, relax by a stocked pond (no license needed), or fish in our stocked trout stream. Welcome to your rural retreat!

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Guest favorite

An outdoor pool reflects the surrounding trees and distant mountains under a clear blue sky. Soft sunlight bathes the scene, emphasizing the serene landscape. The area is tranquil, offering a picturesque view of nature's beauty.

Home in Sperryville

4.92 out of 5 average rating, 92 reviews

Incredible views with hot tub & swimming pool

This modern-rustic cottage overlooks Shenandoah National Park's majestic mountains, offering breathtaking views year round. Escape to a secluded 13-acre wooded property, ideal for families and friend groups. The house features a stunning outdoor pool, hot tub, and fire pit. It offers inviting common spaces for spending time together and private nooks for alone time and work. Pool is open 1st week of April - mid-November, with heating available for colder months. Hot tub is open year-round.

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Top guest favorite

Home in Luray

5.0 out of 5 average rating, 80 reviews

Fall Foliage | HotTub+FirePit+CoffeeBar | Near SNP

Discover a tranquil escape in the heart of Luray, VA — where modern design meets quiet mountain living. This beautifully designed tiny home offers a unique blend of luxury, comfort and nature. What You'll Love: ✨Plush King Bed ✨Full bathroom with rain shower ✨Sleek, full-sized kitchen with modern appliances & all the essentials ✨Specialty, fully stocked coffee & tea bar complete with recipes ✨Large windows with forest views & private back deck ✨Cold plunge, pool & hot tub with views

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Top guest favorite

A log home with multiple gables is situated on a green hillside, featuring a wide deck and large windows. A crystal-clear pool is shown in the foreground, surrounded by lounge chairs and colorful inflatables, with a hot tub visible nearby, all under a partly cloudy sky.

Guest suite in Ruckersville

4.94 out of 5 average rating, 84 reviews

Cornerstone Farms

Mountain Rustic Elegance describes this clean fully furnished, 1 bedroom apartment in a log home on 80 acres in Greene County with 1 Queen bed, 1 pull out Queen sofa and a rollaway bed (on-demand ),with a fully equipped kitchen,full bath with washer and dryer. Amenities: Dry sauna inside, pool table, foosball table and board games in the closet. Outside: large pool, fire pit, hot tub, Grill. Enjoy eating outside as you soak in the beautiful sunset views while you sit relax and unwind.

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Top guest favorite

A private deck offers unobstructed views of rolling hills and distant mountains, framed by bare trees and open fields. The white railing complements the natural landscape, creating a serene outdoor space to enjoy the surrounding scenery.

Cottage in Stanardsville

4.95 out of 5 average rating, 302 reviews

Farm Studio with Blue Ridge views 15 mins from SNP

The Carriage House Studio is perfect for a romantic getaway or quiet escape. Enjoy stunning mountain views from the deck. Hike our private trails. Fish in pond or South River. Enjoy pool. Delight in farm animals including our miniature horses. Less than 20 mins from Shenandoah National Park and Appalachian Trail. Located 2 hours southwest of Washington, DC; 1 1/2 hours east of Richmond; and 25 minutes north of Charlottesville, VA. Near wineries; Monticello, Montpelier, Ash Lawn, and UVA.

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Guest favorite

An open living area features high wooden ceilings with exposed beams, creating a spacious atmosphere. A large kitchen island with bar seating is situated near a dining table. Two spiral staircases lead to upper levels, while large windows frame views of the surrounding nature.

Home in Robertson

4.93 out of 5 average rating, 259 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.

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A renovated 1920s farm cottage sits on expansive green lawns, surrounded by lush vegetation and distant hills. A wooden deck wraps around the front, providing outdoor seating space. The structure features a gabled roof and large windows that invite natural light.

Home in Syria

4.76 out of 5 average rating, 17 reviews

Pete's Farm Cottage - on Graves Mountain Farm

Sitting on the lawns of Graves Mountain Farm & Lodges, this is a renovated 1920's farm cottage with three bedrooms, sleeping 8 in 2 bedrooms with 1 Queen each and one attic bedroom with 1 queen and 2 twins. The cottage has NO kitchen, but does have a refrigerator, microwave and coffee maker. The Farmhouse Restaurant is just a short walk up the hill to the Main Lodge. Prepared meals at Market, Deli & Tackle. Gas grill, fire circle on grass. WIFI, satellite TV. Seasonal pool nearby.

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