Vacation rentals with a pool in Charlottesville

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Charlottesville

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

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Guest favourite
An open living and dining area is displayed, featuring a wooden dining table set with decorative placemats. A comfortable seating arrangement is visible in the background, alongside a console table and artwork on the walls. Natural light enters through sliding glass doors.
Guesthouse in Afton
4.99 out of 5 average rating, 285 reviews

Mountain Cottage, Swimming Pool, Views, Nelson 151

Wake to gorgeous Mountain views & rolling green meadows bordering the Rockfish River on our family estate. Private attached unit with built in pool (mid April-mid Sept)in the Blue Ridge mountains of Nelson County Virginia on the center of the 151 Brew Ridge Trail. Much preparation has gone into making your stay beautiful, convenient and comfy. No need to physically interact if that’s your desire. Enjoy swimming, hiking, kayaking, horse back riding, skiing, snowboarding, and more! 3 nite minimum

Top guest favourite
Cabin in Dayton
4.99 out of 5 average rating, 205 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!

Top guest favourite
A wooden walkway leads to the entrance of the house, framed by vibrant pink rhododendron flowers. Tall trees provide a natural backdrop, with dappled sunlight filtering through the leaves, creating a serene outdoor setting.
Home in Wintergreen Resort
4.94 out of 5 average rating, 145 reviews

Bear's Mountain Escape

Dog friendly, 3 BR, 2 BA, loft style condo located in the heart of the Wintergreen Resort. Ski check-in, restaurants, the mountaintop market, & The Mountain Inn are all right across the street! 2-story unit with a main floor primary BR & hall bath. Main floor bonus room with single & trundle. The loft contains 2 twin beds and the 2nd full bath. Parking, pool, washer/dryer, and Wi-Fi included. Fully stocked kitchen, wood burning fireplace, balcony, all towels/linens provided. Sleeps up to six.

Guest favourite
A sweeping landscape showcases rolling green hills under a partly cloudy sky. Tree-lined fields extend towards a winding road that leads to nearby structures, set amidst nature's tranquility.
Farm stay in Charlottesville
4.9 out of 5 average rating, 174 reviews

Jefferson Cottage quiet farm close to everything

The cottage circa 1802 offer a peaceful private setting on a historic horse farm once part of Monticello with close proximity to wineries (10 minutes), town (12 minutes), Rivanna River borders the property, Carter mountain (8 minutes) and many other activities. A "Jimmy Buffet" salt water pool complex has a private Jacuzzi for each unit, double bars, two fire pits, frig ,full bath/shower/changing room) There is a private lake (catch and release fishing) and many places to walk on the property.

Top guest favourite
A historic two-story estate is visible beyond a cobblestone driveway, framed by lush green trees. In the foreground, a stone statue of a dog holds a basket of fruit, adding charm to the property entrance against a clear blue sky.
Home in Charlottesville
4.98 out of 5 average rating, 110 reviews

Rivanna Farm Estate North I Pickleball I Pool

This historic 42-acre country estate features four distinct residences, three of which are Airbnb rentals. The "North” offers beautiful views of the Blue Ridge Mountains and includes 4 bedrooms: 2 bedrooms with queen beds, and another with 2 twin beds on the main floor, and an additional queen bedroom upstairs. The second floor has a full kitchen, living room, & dining area. On the lower level is a yoga studio, game room, outdoor patio area w/seating, and charcoal bbq. (Charcoal not provided)

Top guest favourite
A serene landscape showcases expansive green fields, framed by rolling hills and colorful autumn foliage. Majestic mountains rise in the distance under a clear blue sky, creating a peaceful and inviting natural setting.
Guesthouse in Charlottesville
5 out of 5 average rating, 128 reviews

Hidden Gem near town and Monticello with a pool

We call this our hidden gem because it's not too far from town, wineries, UVA, Monticello and more that Charlottesville has to offer, but yet it's far enough away from the hustle and bustle. The renowned Clifton Inn, a popular destination wedding venue is less that 1/4 mile away. Thomas Jefferson's Monticello is a 7 minute drive. The campus of UVA is a 15 minute drive. We call this our studio loft because it has the feel of a mountain cabin. The views are gorgeous and the setting is peaceful.

Guest favourite
The exterior of La Petite Maison showcases a charming guest house with a large screened porch, surrounded by vibrant flower beds. A turquoise umbrella shades a lounge chair next to the seasonal in-ground pool, providing a relaxing outdoor space.
Guesthouse in Gordonsville
4.9 out of 5 average rating, 190 reviews

La Petite Maison at Hedgeapple Hollow

La Petite Maison (our guest house) is the perfect place to simply get away from the hustle and bustle and relax! Sit in the private screen porch and watch the sun melt into the mountains. Deer, hummingbirds, bluebirds, and the occasional turkey like to hang out on the 8 acres of the property, perfect for any wildlife lover. Enjoy the fenced in common area featuring a seasonal in-ground pool. Conveniently situated near award-winning wineries, Montpelier, and historic downtown Gordonsville.

Top guest favourite
The image showcases a grand brick Victorian house surrounded by lush greenery. A well-maintained pathway leads to the entrance, flanked by dense shrubs. The sky is bright, with a few clouds visible above the distinctive architectural features of the home's multiple gables and turrets.
Apartment in North Downtown
4.95 out of 5 average rating, 105 reviews

Private Apt in Historic C'ville Home (Lane Side)

Looking for a place in C'ville close to everything? Look no further. This newly furnished apartment, which comes with high speed internet, a Smart TV, and access to a swimming pool, is just a short walk away to the Historic Downtown Mall. It is a short 5 minute drive to the UVA hospital/campus, and is within reasonable driving distance to the area's many wineries and breweries. Nestled in the heart of the city, and attached to a historic C'ville home, this apt is an excellent place to stay.

Top guest favourite
The exterior of the home is illuminated by soft lights, creating a warm atmosphere at night. The backyard features two swimming pools adjacent to a concrete deck with various seating options. Tall trees provide a serene backdrop to the scene.
Apartment in Palmyra
4.99 out of 5 average rating, 130 reviews

Love 2B close 2U: Quiet, comfy Apartment & Pool!

Quiet, rural setting in neighborhood culdesac. Located off Rt 53, approx 15 mins from Monticello & FUMA. Basement of home, w/private entrance is a 1000 square foot apartment with a large full bathroom, large bedroom with 2 Queen size beds, open floor plan with living, dining area and kitchen. Space includes a large screened in porch w/ bed swing, patio area & swimming pool. No diving - deep end 6ft. View of woods on back of property w/ sunrise through the trees in morning. Lovely retreat.

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
A bright and airy living area is highlighted by large windows offering mountain views. A casual seating arrangement features a light-colored sofa and a wooden dining table surrounded by black chairs. Sliding glass doors provide access to an outdoor deck.
Apartment in Rockfish
4.98 out of 5 average rating, 218 reviews

Blue Ridge Bliss - For family & friends to enjoy!

Welcome to Blue Ridge Bliss! Come enjoy the mesmerizing mountain top views of this well-appointed condo in The Ledges of Wintergreen Resort. It’s the perfect place to unwind, unplug and recharge. Whether here to ski, hike, or visit Virginia wineries, cideries, or craft breweries you’re sure to enjoy the beautiful views from the living room and deck. A short walk to The Highlands lift and across the street from Fire & Frost eatery and the Wintergreen Spa, this is an ideal location.

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.

Popular amenities for Charlottesville rentals with a pool

When is the best time to visit Charlottesville?

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Quick stats about vacation rentals with a pool in Charlottesville

  • Total vacation rentals

    Explore 60 vacation rentals in Charlottesville

  • Nightly prices starting at

    Charlottesville vacation rentals start at $55 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,150 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    60 of Charlottesville vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Charlottesville rentals

  • 4.7 Average rating

    Charlottesville stays receive an average rating of 4.7 out of 5 from guests

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