
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.

Historic Log Farmhouse Suite 2 - 2 Bedrm, 3 Bed
Historic early 1800s log farmhouse suite. Renovated - downstairs a sitting room with large fireplace, full bath (shower) and one KING bedroom, upstairs - second bedroom with 1 QN and 1 TWIN and half bath. Big shared porch w/ rocking chairs in front. Nr pool, short walk to Main Lodge & Farm Restaurant. Cleaning Fee additional $50 per stay. Pet Fee- $35 per stay. 1800 acres to explore- 18 mi of trails, 2 fishing streams, 2 ponds, Farm to Table Restaurant, Market-Deli & Tackle with meals to go.

Farm Cottage w. Blue Ridge views 20 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 - Birdwatchersโ 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.

Wild Wind Cottage - On Robinson River Trout Stream
Our cabin, built in the early 1900s was the local one room schoolhouse. Converted from its days of desks and pencils, it sleeps six and has one bedroom with queen bed, one annex bedroom with two bunk beds and also two bunk beds to the side of the living area. Tech UNPLUGGED. Thatโs the way it is in our valley. No cell, little Internet. For basic not streaming connection, please come to our Lodge, 2 miles upstream or to our the local village mercantile. Pet friendly - additional $25 per night

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*

"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

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 20 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.

Brewery Manor Sleeps 10 Hot Tub
Woodbourne Estate, circa 1810, is a National and Virginia historic registered landmark Manor House and farm nestled in the foothills of the Blue Ridge Mountains in Madison, Virginia. The 53-acre Estate is also home to our award-winning Bald Top Brewing Company which sits just a comfortable stroll beyond the Manor house. This magical Manor, with its gorgeous grounds, gardens, barns, ruins, pool, stream and vistas awaits! The Manor at Bald Top: Drink in the Moment!
Popular amenities for Madison County rentals with a pool
House rentals with a pool

Pete's Farm Cottage - on Graves Mountain Farm

"Country Living at It's Finest"

The River House at the Swinging Bridge

Incredible views with hot tub & swimming pool

The River House with the River Deck

Farm Cottage w. Blue Ridge views 20 mins from SNP

Kite House in the Blue Ridge Mountains by S.N.P.

One Of A Kind Home in VA Wine Country on 50 acres
Other vacation rentals with a pool

Valley View Cottage in the Blue Ridge Mountains

Redwood 2 Condo Graves Mountain Farm in Blue Ridge

Dogwood Cottage by Shenandoah Park

Boxwood Cottage - Shenandoah National Park

Honeysuckle Farm - Secluded Luxury - 700 acres

Peon Palace Cottage on Rose River by Blue Ridge

Greenwood - near Old Rag & White Oak Canyon Trails

Blackwood - Valley of Rose River by the Blue Ridge
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- Shenandoah National Park
- Luray Caverns
- Lake Anna State Park
- Bryce Resort
- University of Virginia
- Early Mountain Winery
- Jiffy Lube Live
- Monticello
- James Madison University
- Glass House Winery
- Cardinal Point Winery
- Blenheim Vineyards
- Prince Michel Winery
- Shenandoah River Outfitters
- The Rotunda
- Frontier Culture Museum
- John Paul Jones Arena
- James Monroe's Highland
- Downtown Mall
- Shenandoah Caverns
- Sky Meadows State Park
- White Oak Lavender Farm & The Purple WOLF Vineyard
- Grand Caverns
- IX Art Park





