
Vacation rentals with a pool in Charlottesville
Find and book unique homes with a pool on Airbnb
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 G$8,354 GYD 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
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

Rivanna Farm Estate North I Pickleball I Pool
Set on a historic 42-acre country estate, the “North” is one of three Airbnb guest homes located on the property, alongside our private residence. Enjoy sweeping views of the Blue Ridge Mountains which accommodates 8 guests with 4 bedrooms: 2 queen bedrooms, one bedroom with 2 twin beds and a queen bedroom upstairs. The second floor features a fully equipped kitchen, living room, and dining area. On the lower level is a yoga studio, game room, and access to an outdoor patio w/ charcoal grill.

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.

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.

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.

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.

151Escape | 5☆ Group Fun! Game Room/Bar/Deck/4kTVs
Enjoy mountain adventures with friends & family at this beautiful & newly renovated 5 bedroom mountain house ideally located in Virginia Wine Country at Wintergreen Resort’s Stoney Creek valley area. This amazing home features: - 75” & 55” 4k TVs - Fully equipped, live edge wet bar & bar countertop - Professional Ping Pong table - Deck with views, firepit & grill Just minutes from skiing, golf, hiking, wineries, breweries, apple-picking and other adventures the area offers all year long!

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.

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.

Beaver Pond Farm - Near Charlottesville
Relax at this unique and tranquil getaway. Sit on the screened in porch and enjoy the sights and sounds of nature while you enjoy a beverage. Visit the Downtown Mall, Monticello, a Winery, a Brewery, or UVA (20 min). Enjoy a dip in the pool (JUN-AUG) or relax by the firepit - perhaps joined by a Great Pyrenees for cocktails. Feel like staying in - SmartTVs with YouTubeTV (which includes local channels) and Gig-speed Internet await. Easy checkout. No cleaning fee.

Mountain Bauhaus | Sleeps 8 | Amenities | Grill
Welcome to your newly decorated and upgraded home in the Blue Ridge Mountains at Wintergreen Resort! A bright and welcoming feel will let you settle in and relax in no time. This space is perfect for families, groups, couples, and adventurous souls who want to explore the mountains or take in the beautiful mountain scenery. Please be sure the read below for Wintergreen Resort Amenities rules and accessibility during your stay.
Popular amenities for Charlottesville rentals with a pool
House rentals with a pool

Cliffs Edge -A Contemporary Mountain Home

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

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

Private Pool Opens April 1 - All Year Hot Tub

Top Shenandoah Stay w/ Pool Access & Firepit

Secluded Lakefront | Private Pool | Dock | Hot Tub

Bear's Mountain Escape

Hottub Ski InOut Renovated Chalet Lower Tyro Slope
Condo rentals with a pool

Where the Trail Ends

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

Panoramic Peak: Wintergreen Condo with Views

Tips Up: Cozy Slopeside Retreat w/ Fireplace

Ski-in/Ski-out Wintergreen Highlands Condo -Views!

2-min drive to resort, Outdoor HOA pool now open!

Cozy Comfort with a View - Wintergreen Resort

Panoramic Sunsets Mountain Views Pool $99 Midweek
Other vacation rentals with a pool

Luxurious Cabin By the Creek! Inground pool! Spa!

Tumnus MTN Cabin *POOL*pvt HOT tub *SNP*FarmTours

The Apartment at Dark Run Retreat

Cozy Cabin+Walk to Ski *Hot Tub* Mtn Vibe

Moonfire Farm cozy Shenandoah Region Getaway

Blue Ridge Bliss - For family & friends to enjoy!

La Petite Maison at Hedgeapple Hollow

NO STEP ENTRY Wintergreen Mtn Home,HotTub,Sleeps10
When is the best time to visit Charlottesville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$26,107 GYD | G$26,943 GYD | G$27,778 GYD | G$26,525 GYD | G$26,943 GYD | G$26,525 GYD | G$26,316 GYD | G$23,810 GYD | G$33,626 GYD | G$39,474 GYD | G$35,715 GYD | G$26,943 GYD |
| 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 |
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- Shenandoah National Park
- Luray Caverns
- Lake Anna State Park
- University of Virginia
- Early Mountain Winery
- Wintergreen Resort
- Monticello
- James Madison University
- Devils Backbone Brewing Co Basecamp
- Glass House Winery
- Cardinal Point Winery
- Blenheim Vineyards
- Prince Michel Winery
- The Rotunda
- Frontier Culture Museum
- John Paul Jones Arena
- James Monroe's Highland
- Downtown Mall
- Shenandoah Caverns
- White Oak Lavender Farm & The Purple WOLF Vineyard
- Grand Caverns
- IX Art Park
- James River State Park
- Massanutten Indoor WaterPark





