
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.

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

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!

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.

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.

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)

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.

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.

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.

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.

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.

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.

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
House rentals with a pool

Luxury Retreat~Hot Tub~Sauna~Game Rm~2 King Suites

Makin' Mountain Memories Jacuzzi, Game room, Dogs!

Top 1% Shenandoah Getaway | 4BR w/ 2 King Suites

Peaceful 3-BR Mountain home w/Fireplace + Hot tub

Hottub Ski InOut Renovated Chalet Lower Tyro Slope

Misty Mountain Cabin w/spa

Cozy Mountain Home Nestled in Nature!

Peaceful Cottage
Condo rentals with a pool

The Modern Mountain Condo

Blue Ridge Retreat: Your Cozy Mountain Getaway

Ski-In Ski-Out ~ Mtn Views ~ King Suite

Five Minute Walk to Everything!

Eight Minute Walk to Everything

Panoramic Peak: Wintergreen Condo with Views

Tips Up: Cozy Slopeside Retreat w/ Fireplace

2-min drive to resort, stair-free/free firewood!
Other vacation rentals with a pool

Suite August- Charlottesville

Private Studio Apt Retreat

Arrowhead Cabin - Cabin with Pool! 10 mins to UVA

On Cottonwood Pond

The Franklin Estate - Suite F-Private Apt-King Bed

Hot Tub, Heated Pool 180-Mt View Pvt Retreat

Designer Home w/ Incredible Views, Sleeps 16

Luxurious Keswick guest house with pool
When is the best time to visit Charlottesville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $160 CAD | $152 CAD | $177 CAD | $175 CAD | $178 CAD | $175 CAD | $174 CAD | $157 CAD | $222 CAD | $261 CAD | $236 CAD | $178 CAD |
| Avg. temp | 2 °C | 4 °C | 8 °C | 14 °C | 18 °C | 22 °C | 24 °C | 23 °C | 20 °C | 14 °C | 9 °C | 4 °C |
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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- Shenandoah National Park
- Luray Caverns
- Early Mountain Winery
- University of Virginia
- Downtown Mall
- Lake Anna State Park
- James Monroe's Highland
- Wintergreen Resort
- Prince Michel Winery
- Frontier Culture Museum
- Blenheim Vineyards
- Devils Backbone Brewing Co Basecamp
- Cardinal Point Winery
- John Paul Jones Arena
- Monticello
- Glass House Winery
- James Madison University
- The Rotunda
- Grand Caverns
- White Lotus Eco Spa Retreat
- Cooter's Place
- James Madison's Montpelier
- IX Art Park
- James River State Park




