Vacation rentals with a pool in Madison County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Madison County

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Bungalow in Stanardsville

4.93 out of 5 average rating, 241 reviews

Romantic, Carriage House Studio at Fairhill Farm

Delight in the bold views of the Blue Ridge Mountains while lounging on your private deck at the Carriage House on Fairhill Farm. Spring has sprung. We are open. Stroll on 300 acres Hike our private trails. Fish in private pond or river. Enjoy pool. Delight in farm animals including our miniature horses. Located 2 hours southwest of Washington, DC, 1 1/2 hours east of Richmond and 25 minutes north of Charlottesville, VA. Near Shenandoah National Park, Monticello, Montpelier,Ash Lawn, and UVA

Mar 28 – Apr 4

G$33,248 GYD per night

Guest favorite

Apartment in Madison

4.9 out of 5 average rating, 229 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*

Jun 17 – 24

G$17,074 GYD per night

Guest favorite

Apartment in Ruckersville

4.98 out of 5 average rating, 115 reviews

Historic Estate: The Carriage House Near C'ville

One of the Historic Southern sporting Estates has been a 5* destination for the past five years for overnight stays, weddings, and events. We would be delighted to welcome you to the Carriage House, Pool House, or The Cottage. (Listed separately) Located on a 550-acre estate with 9+ miles of woodland trails with spectacular views of the Blue Ridge Mountains. Work or relax with our High-Speed Internet, two tournament pickleball courts, saltwater pool, or swim in our natural spring-fed lake.

Nov 28 – Dec 5

G$43,293 GYD per night

Guest favorite

Home in Aroda

4.98 out of 5 average rating, 56 reviews

Sunset Retreat a cabin off the beaten path

Relaxation and quiet are two words that come to mind at Sunset Retreat. Close enough to stores for convenience but far enough away for solitude. Large yard, fire pit and concrete area if children want to create a masterpiece in chalk, there is also a tree swing next to woods. Close to many wineries, breweries and hiking. No WIFI or satellite tv, we have antenna only. You are welcome to bring your own hotspot . We have one smart tv. There is also a private in ground pool for summer time use.

Sep 2 – 9

G$30,865 GYD per night

Guest favorite

Guest suite in Ruckersville

4.96 out of 5 average rating, 55 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.

May 22 – 29

G$43,719 GYD per night

Guest favorite

Home in Boston

4.97 out of 5 average rating, 118 reviews

Peacefield - Blue Ridge views near Culpeper

Welcome to the Peacefield! This retreat is nestled in the rolling foothills of the Blue Ridge Mountains in the shadow of Old Rag, overlooking Hazel River Farm (160 acres). The spacious estate is perfect for escaping the city. There are many options for relaxing with a deck, hot tub, pool (summer only), home theater, and an open kitchen connecting the dining and family rooms. The beauty of the estate includes walking trails, glimpses of sheep, and local art (watercolor and photography).

Aug 22 – 29

G$97,268 GYD per night

Guest favorite

Home in Robertson

4.92 out of 5 average rating, 184 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.

Feb 11 – 18

G$139,911 GYD per night

Guest favorite

Farm stay in Madison

4.99 out of 5 average rating, 146 reviews

The Farmhouse at Beautiful Run

We are a small farm with chickens, horses, labs, and red angus. Enjoy a complimentary breakfast each morning! The pool house has a kitchenette-microwave, full size fridge, sink, hot plate, BBQ with a side burner. Fish by the edge of the pond, feed treats to the horses over the fence, hike our 3 miles of trails. We are on FB The Farmhouse at Beautiful Run. Note: we live in a wing of the house, but you will have the main house to yourselves excluding the main kitchen.

Jan 8 – 13

G$142,855 GYD per night

Guest favorite

Farm stay in Luray

4.95 out of 5 average rating, 66 reviews

Beckon Hollow Farm; modern farmhouse on 70 acres

Share in our dream come true! From the comfort of the just-renovated modern farm house, enjoy the calm and quiet of our 70-acre farm at the base of Shenandoah National Park 10 minutes from quaint town of Luray, Luray Caverns, and hikes in the Shenandoah Coffee with a view of mountains in every direction Enjoy the pool in Summer and sledding in Winter Sip wine at the fire in the evening and watch for shooting stars Family-friendly house with toys and bunk beds for kids

Jan 10 – 17

G$96,514 GYD per night

Superhost

Farm stay in Madison

4.96 out of 5 average rating, 98 reviews

VIP Brewery Manor House, Sleeps 10, Heated Pool

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!

Jun 7 – 14

G$110,469 GYD per night

Superhost

Home in Madison

4.92 out of 5 average rating, 77 reviews

The River House at the Swinging Bridge

The River House at the Swinging Bridge is a 13 acre property which includes a 2 acre fenced compound ideal for gatherings of families or friends. With 1000 feet of Robinson river frontage, a private wood to walk in, a Caldera salt water hot tub, a wood-burning sauna, a natural swimming pool, and plenty of games and gathering places, one need not leave the property to enjoy oneself. But hiking and biking trails abound, and breweries and vineyards are minutes away.

Jan 1 – 8

G$126,239 GYD per night

Cottage in Reva

4.78 out of 5 average rating, 23 reviews

AJ's House: Beautiful, Cozy, Renovated! 135/nt

Aunt Judy's House (AJ's) is a 19th- century cottage completely renovated in 2015. The views of sunsets, Blue Ridge Mtns and cattle across the fence will encourage you not to leave the porch. But should you decide to wander you will find hiking, history, excellent dining and a multitude of wineries within a 10 to 40 min. drive. Some guests never get off the porch as the stress of everyday life just melts away.

Aug 19 – 26

G$30,267 GYD per night