Vacation rentals with a pool in Madison County

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.

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.

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.

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*

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!

"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

Honeysuckle Farm - Secluded Luxury - 700 acres

In our completely renovated luxury farmhouse - an isolation experience on 700 acres. 1880s Farmhouse with incredible Blue Ridge views, cattle in the meadows, pond out front. Front and back porches plus a screened porch. Plus Adirondack chair pond overlook. 3 Porches - one screened. Master bedroom on ground floor with King four poster and full bath. non working fireplace. Upstairs, a second master King suite plus 2 bedrooms with two QNS each. Views of surrounding meadows and mountains. .

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.

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.

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.

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.

The River House with the River Deck

The River House with the River Deck is ideal for gatherings of families or friends. Boasting a 3 bedroom 1790's farmhouse, 3 additional sleeping bungalows, a game/movie room, a covered fire pit, a private woods, a salt water hot tub, a wood burning sauna, a natural swimming pool, 1000" of river frontage, and plenty of games and additional amenities, one need not leave the property to enjoy oneself. But hiking and biking trails abound, and breweries and vineyards are minutes away.