
Holiday 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

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.

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.

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!

Yurt*FARM*horses*goats*woods*STARS*Hotub*Hiking
Come experience living in a round structure filled with amenities-fully equipped kitchen, deep tub, heating and AC, hot tub and in-ground pool. Great for couples, friends, and families. A 10 minute hike gets you into Shenandoah National Park, explore our 58 acres on numerous walking trails, visit Charlottesville, historical sites, caves, or play in rivers. Child friendly- no pets.( PRIVATE hot tub Nov 20- March 1.) Check out Cair Paravel Farmstead on FB/the web to see all we have to offer.

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.

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.

Moonfire Farm cozy Shenandoah Region Getaway
Experience charm and nature at Moonfire Farm! Our finished basement on a 5-acre hobby farm offers delightful animal encounters with chickens, ducks, alpacas, and hilarious goats. Our active family of three, including our 7-year-old daughter Piper, welcomes you. High-speed Internet and nearby wineries, breweries, hiking trails, and pick-your-own fruit locations await you. Explore our guidebook for recommendations. Book now for a memorable farm getaway!
Popular amenities for Charlottesville rentals with a pool
House rentals with a pool

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

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

Makin' Mountain Memories Jacuzzi, Fire pit, Grill

Top 1% Shenandoah Family Vacation w/ Pool Access

Bear's Mountain Escape

Downtown Riverview Castle with Pool and Hot Tub!

Hottub Ski InOut Renovated Chalet Lower Tyro Slope

Cozy Mountain Home Nestled in Nature!
Apartment rentals with a pool

The Modern Mountain Condo

Blue Ridge Retreat: Your Cozy Mountain Getaway

Five Minute Walk to Everything!

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

Eight Minute Walk to Everything

Panoramic Peak: Wintergreen Condo with Views

Panoramic Views | Sunrise on the Deck | Nelson 151

Tips Up: Cozy Slopeside Retreat w/ Fireplace
Other holiday rentals with a pool

Appleberry Mountain Cottage

On Cottonwood Pond

Luxe Farm Retreat with Pool & Hot Tub

Historic Bloomingdale Farmhouse w/Mountain Views

Luxurious Keswick guest house with pool

La Petite Maison at Hedgeapple Hollow

Overlook 180 degree views w/Peloton!

Brewery Manor Sleeps 10 Hot Tub
When is the best time to visit Charlottesville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £92 | £95 | £98 | £93 | £95 | £93 | £93 | £84 | £118 | £139 | £126 | £95 |
| 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 holiday rentals with a pool in Charlottesville

Total holiday rentals
Explore 60 holiday rentals in Charlottesville

Nightly prices starting at
Charlottesville holiday rentals start at £29 per night before taxes and fees

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

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
60 of Charlottesville holiday 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
- University of Virginia
- Early Mountain Winery
- 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
- James Madison University
- Glass House Winery
- The Rotunda
- Grand Caverns
- James Madison's Montpelier
- White Lotus Eco Spa Retreat
- White Oak Lavender Farm & The Purple WOLF Vineyard
- IX Art Park
- Massanutten Indoor WaterPark





