
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.

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.

Twin Ponds | King Beds, Hot tub, Game Room, 75" TV
Welcome to Twin Ponds, a beautifully appointed & fun-filled mountain house in Wintergreen Resort's Stoney Creek just minutes from Rt 151’s breweries & wineries, golf, Lake Monocan, skiing, hiking & more. This 4-bedroom, 3.5-bathroom home features: - 3 king & 2 queen beds - Amazing Game Room w/ premium air hockey, ping pong, foosball, shuffleboard, board games, game table & 75" 4k Roku TV - Deck w/ 36" Blackstone flattop grill, gas firepit, cafe lights & hot tub We look forward to hosting you!

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)

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.

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.

Game Room+Screen Porch+King Beds+Hot Tub on 151
Luxury meets location at this spacious golf-course retreat—minutes to Nelson 151’s vineyards, breweries, and hiking. Fun for adults & kids with garage game room, board games and books. Enjoy summer fun with screened porch, BBQ, lawn games, and gas fire pit. Great layout for groups and families. 2 King beds, 1 Queen, 2 Doubles. EV charger Community pool access Discounted weekly/monthly stays, and just 35 mins to UVA.
Popular amenities for Charlottesville rentals with a pool
House rentals with a pool

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

Guests Rave! Shenandoah Retreat w/ Pool Access

Makin' Mountain Memories Jacuzzi, Fire pit, Grill

HUGE Mountain Lodge! Hot Tub, Fire Pit, Game Room!

Bear's Mountain Escape

Cozy Mountain Home Nestled in Nature!

Peaceful Cottage

Wintergreen Resort | Pool, Hike, Golf, Hot Tub,
Apartment rentals with a pool

Where the Trail Ends

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

Tips Up: Cozy Slopeside Retreat w/ Fireplace

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

Private Studio Apt Retreat

On Cottonwood Pond

Unique OASIS - Silo Barn - Swim Pond- 5 Miles Trai

Heated Pool+Hot Tub | 2BR Mt View Farm Retreat

Historic Bloomingdale Farmhouse w/Mountain Views

UVA Graduation Retreat w/ Pool Near C’ville

NO STEP ENTRY Wintergreen Mtn Home,HotTub,Sleeps10

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 | £93 | £96 | £99 | £95 | £96 | £95 | £94 | £85 | £120 | £141 | £127 | £96 |
| 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 £30 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
- Massanutten Resort
- Lake Anna State Park
- Early Mountain Winery
- University of Virginia
- Downtown Mall
- Wintergreen Resort
- Devils Backbone Brewing Co Basecamp
- James Monroe's Highland
- Prince Michel Winery
- Blenheim Vineyards
- Cardinal Point Winery
- Monticello
- Glass House Winery
- Frontier Culture Museum
- John Paul Jones Arena
- James Madison University
- The Plunge Snow Tubing Park
- The Rotunda
- White Oak Lavender Farm & The Purple WOLF Vineyard
- Grand Caverns
- IX Art Park
- White Lotus Eco Spa Retreat





