
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.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Charlottesville rentals with a pool
House rentals with a pool

Peacefield - Blue Ridge views near Culpeper

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

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

All-Year Heated Covered Private Pool / Hot Tub

Farmhouse on Working Vineyard

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

Bear's Mountain Escape

Hottub Ski In/Ski Out Renovated Chalet Lower Tyro
Condo rentals with a pool

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

Five Minute Walk to Everything!

Eight Minute Walk to Everything

Buena Vista Panoramic Retreat: Million Dollar View

Massanutten Woodstone 2-BR, 2 Bath

Tips Up: Cozy Slopeside Retreat w/ Fireplace

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

Cozy, clean, quiet mountain condo- King bed
Other vacation rentals with a pool

3Bdrm | Hot tub, Firepit, Wineries | 9miles to UVA

Suite August- Charlottesville

The Red Cabin at Estouteville Farm

Mountain View Nest

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

Charming Cottage on Historic 1780’s Farm

Pool, Hot Tub - Mt Views near Vineyards, Hiking

NO STEP ENTRY Wintergreen Mtn Home,HotTub,Sleeps10
Quick stats about vacation rentals with a pool in Charlottesville
Total rentals
50 properties
Nightly prices starting at
$56 CAD before taxes and fees
Total number of reviews
950 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Rentals with outdoor seating Charlottesville
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- Rentals with pools Albemarle County
- Rentals with pools Virginia
- Rentals with pools United States
- Massanutten Resort
- Luray Caverns
- Early Mountain Winery
- Lake Anna State Park
- Ash Lawn-Highland
- Prince Michel Winery
- The Foundry Golf Club
- Hermitage Country Club
- Chisholm Vineyards at Adventure Farm
- Massanutten Ski Resort
- Frontier Culture Museum
- Spring Creek Golf Club
- Car and Carriage Caravan Museum
- The Plunge Snow Tubing Park
- Wintergreen Resort
- Blenheim Vineyards
- Birdwood Golf Course
- Farmington Country Club
- Glass House Winery
- Little Washington Winery
- Cardinal Point Winery
- Burnley Vineyards
- Meriwether Springs Vineyard and Brewery