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
Home in Stanardsville
4.98 out of 5 average rating, 135 reviewsCharming Carrie's Cottage at Fairhill Farm
Jan. 4 – 11
Home in Robertson
4.92 out of 5 average rating, 182 reviewsOne Of A Kind Home in VA Wine Country on 50 acres
Feb. 11 – 18
Home in Lovingston
4.95 out of 5 average rating, 175 reviewsCottage on The Knoll *heated pool open May 17*
Oct. 20 – 27
Home in Afton
4.94 out of 5 average rating, 133 reviewsFarmhouse on Working Vineyard
Jan. 1 – 8
Home in Lovingston
4.85 out of 5 average rating, 280 reviewsSecluded Mountain Cabin w/ Pool, Trails & Winery ❤️
Jan. 19 – 26
Home in Boston
4.97 out of 5 average rating, 118 reviewsPeacefield - Blue Ridge views near Culpeper
Oct. 11 – 18
Home in Lyndhurst
4.97 out of 5 average rating, 99 reviewsOak Tree Cottage - beautiful farm, mountain views.
Jan. 13 – 20
Home in Wintergreen Resort
4.97 out of 5 average rating, 153 reviewsSki-In/Ski-Out Renovated Chalet on Lower Tyro
Dec. 7 – 14
Condo rentals with a pool
Condo in Wintergreen Resort
4.99 out of 5 average rating, 175 reviewsCozy getaway w/ heated floors, dog friendly
Aug. 6 – 13
Condo in Wintergreen Resort
4.91 out of 5 average rating, 179 reviewsA True Mountain Getaway! Ski in/Ski out!
Jan. 2 – 9
Condo in Wintergreen Resort
4.94 out of 5 average rating, 225 reviewsCozy, clean mountain condo- King bed, dog friendly
Dec. 27 – Jan. 3
Condo in Wintergreen Resort
4.9 out of 5 average rating, 101 reviewsTips Up: Cozy Slopeside Retreat w/ Fireplace
Jun. 14 – 21
Condo in Wintergreen Resort
4.95 out of 5 average rating, 173 reviewsNew Construction! 1 Bed/2 Bath, pet friendly
Aug. 30 – Sep. 6
Condo in Wintergreen Resort
5.0 out of 5 average rating, 166 reviewsWintergreen: Mountain View for Miles Sunset Vista
Jul. 11 – 18
Condo in Wintergreen Resort
4.96 out of 5 average rating, 154 reviewsThe Modern Mountain Condo
Aug. 24 – 31
Condo in Wintergreen Resort
4.9 out of 5 average rating, 191 reviewsLight Filled Awe-Inspiring Views from Every Window
Oct. 20 – 27
Quick stats about vacation rentals with a pool in Charlottesville
Total rentals
50 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
780 reviews
Nightly prices starting at
$55 CAD before taxes and fees
Destinations to explore
- Richmond Vacation rentals
- Cabins Vacation rentals
- Arlington Vacation rentals
- Alexandria Vacation rentals
- Bethesda Vacation rentals
- Fairfax Vacation rentals
- Shenandoah Vacation rentals
- Capitol Hill Vacation rentals
- Lake Anna Vacation rentals
- Washington Vacation rentals
- Deep Creek Lake Vacation rentals
- Philadelphia Vacation rentals
- Rentals with pools United States
- Rentals with pools Washington
- Rentals with a patio Charlottesville
- Guesthouse rentals Charlottesville
- Monthly Rentals Charlottesville
- Townhouse rentals Charlottesville
- Cottage rentals Charlottesville
- Rentals with outdoor seating Charlottesville
- Rentals with a firepit Charlottesville
- Pet-friendly rentals Charlottesville
- Private suite rentals Charlottesville
- Cabin rentals Charlottesville
- House rentals Charlottesville
- Rentals with breakfast Charlottesville
- Family-friendly rentals Charlottesville
- Rentals with an EV charger Charlottesville
- Apartment rentals Charlottesville
- Condo rentals Charlottesville
- Kid-friendly rentals Charlottesville
- Fitness-friendly rentals Charlottesville
- Rentals with a fireplace Charlottesville
- Rentals with a washer and dryer Charlottesville
- Rentals with pools Virginia
- Rentals with pools Virginia
- Rentals with pools Southern United States
- Rentals with pools Albemarle County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom