
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.

Farmhouse on Working Vineyard
Situated on the east side of the Blue Ridge, this renovated farmhouse in beautiful Nelson County is surrounded by 15 acres of vines and has stunning views of the mountains. The house has all the amenities you could wish for while keeping its charm. The farmhouse is a very private and idyllic residence. There is a front porch with a bench swing and a hammock, as well as a small flagstone patio with wrought iron furniture for your relaxation. The pool is around back and is fenced in. The large deck above the pool is excellent for basking in the sun or watching it set over the mountains. If you run out of wine, you can walk down to the winery's tasting room and stock up, listen to (occasional) live music, or enjoy a bottle on their patio for a change of pace. The beauty of Nelson County and the Cardinal Point Farmhouse will help make your stay one of the most relaxing you could ever imagine. **We do allow pets with an additional charge of $50/day. If you will be bringing your pet, please let us know and we will adjust the price accordingly (airbnb.com does not have an automatic fee to be added on when booking). All parts of the property are accessible EXCEPT THE BARN. This is a working vineyard, so there are tools, equipment and chemicals that are not appropriate for guest access. Someone should be available by phone or in person for any questions or problems you have. Our farmhouse is conveniently located on the same property as our winery(!): www.cardinalpointwinery.com. Also, within a few miles, there are three other wineries, three breweries, a distillery and a cidery. From May through October, nearby Nellysford hosts a phenomenal farmers' market. Charlottesville, with its vibrant arts and restaurant scene is 25 minutes away. On the other side of the Blue Ridge Mountains (just 15 minutes away), you can go to the movies, out to eat, grocery shop, etc in Waynesboro. But, honestly, there is a good chance you may not want to leave our farm at all. There is no public transportation in our area, but there are many services to take guests on winery and brewery tours. They are a great and worry-free way to sample what the area has to offer! As this is a working vineyard, occasionally there may be someone on the premises taking care of the grapes. We will be sure to let you know when someone will be on the property.

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

Private Apt in Historic C'ville Home (Garden Side)
This cozy, newly refurbished, 1 BR/1 Bath, apartment is attached to a historic Charlottesville home. With just a 10 min walk to the Downtown Mall and a short drive to the university hospital/campus, the location is nestled in the heart of C'ville. Special amenities include a Sleep Number bed, fast Wifi, a 50" Smart TV with access to Amazon Prime and Netflix, access to pool use during the summer, and Park Lane street parking. Hand crafted soapstone counters and farm sink, beautiful new tile work.

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)

Tumnus MTN Cabin *POOL*pvt HOT tub *SNP*FarmTours
Recharge Now! Soak in nature, pool, and private spa- lounge in the spacious screened in porch, take a walk in the woods, eat farm fresh food. 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.

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.

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.

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.

Private Pool Opens April 1 - All Year Hot Tub
Experience the Blue Ridge Mountains and country life of central Virginia and enjoy everything Nelson County has to offer. The Cottage on the Knoll is a comfortable 3br/2bth that’s centrally located in Nelson County, offering the perfect mix of modern comfort and country charm. The Nelson 29 and Nelson 151 craft beverage trails await you, while plenty of hiking, fishing, and mountain views will appease any outdoor recreation lover or nature enthusiast, making it the perfect getaway.

Mountain View Getaway Yurt
Come enjoy country living in beautiful western Albemarle county. Our yurt is on a 13 acre property on a quiet country road. (My husband and I also have our home about 200 ft away from yurt). The yurt features a relaxing outdoor claw foot tub/shower with beautiful country views. The private bathroom is situated on the deck of the yurt. The pool is a shared space directly behind our home. The wooded part of the property is private with a beautiful walking trail for you to enjoy.

1 bedroom condo, close to hikes & breweries & pool
Cozy 1BR Wintergreen condo 🌳 🌄 Close to scenic hikes, local breweries and wineries. The resort village, and mountain-top market, just minutes away. Enjoy a fully stocked kitchen, premium coffee and teas, cooking oils and spices. Relax after a day outdoors and enjoy a smart TV, fast WiFi and games. Comfortable queen bed in the bedroom plus new queen sleeper sofa in the living room. Private furnished patio with peaceful wooded views and or cool off in the heated community pool.
Popular amenities for Charlottesville rentals with a pool
House rentals with a pool

Epic Sunrise Views • 2 Decks • Game + Billiards Rm

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

Makin' Mountain Memories Jacuzzi, Game room, Grill

Top 1% Shenandoah Family Vacation w/ Pool Access

Hottub Ski InOut Renovated Chalet Lower Tyro Slope

Cozy Mountain Home Nestled in Nature!

Peaceful Cottage

PetFriendly/HotTub/GameRoom/FirePit/PoolAccess
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

Ski-in/Ski-out Wintergreen Highlands Condo -Views!
Other vacation rentals with a pool

Private Studio Apt Retreat

Appleberry Mountain Cottage

On Cottonwood Pond

GreeneStone A relaxing home Shenandoah NP

Historic Bloomingdale Farmhouse w/Mountain Views

Owl Bnb | Walkable to Slopes | Speakeasy Room

NO STEP ENTRY Wintergreen Mtn Home,HotTub,Sleeps10

Elegant Keswick guest house with luxurious pool
When is the best time to visit Charlottesville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 99 | € 94 | € 110 | € 109 | € 110 | € 109 | € 108 | € 98 | € 138 | € 162 | € 146 | € 110 |
| 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 € 34 per night before taxes and fees

Verified guest reviews
Over 1,140 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
60 of Charlottesville vacation rentals include wi-fi 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
- Wintergreen Resort
- James Monroe's Highland
- Blenheim Vineyards
- Cardinal Point Winery
- Prince Michel Winery
- Devils Backbone Brewing Co Basecamp
- Frontier Culture Museum
- John Paul Jones Arena
- Monticello
- Glass House Winery
- James Madison University
- The Rotunda
- Grand Caverns
- James Madison's Montpelier
- White Lotus Eco Spa Retreat
- IX Art Park
- White Oak Lavender Farm & The Purple WOLF Vineyard
- James River State Park





