
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
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Popular amenities for Charlottesville rentals with a pool
House rentals with a pool

Kismet Cottage | Cville Home with Pool & Mtn Views
We loved using the pool and the patio/grill area. The view and the landscaping are beautiful. The owner was helpful and responsive; she supplied firewood and charcoal. Plenty of dining space both indoors and out. Good A/C.

Mid-Century Modern: Hot Tub~Free Pool Access~Grill
Great mountain house! House was clean and had everything we needed. The host sent us local recommendations and checkin/out was easy!

Peacefield - Blue Ridge views near Culpeper
Fabulously beautiful location. Picturesque. Home was lovely, comfortable and delightful to stay in. Many great places to sit, enjoyable amenities. Host was kind to allow us some flexibility to support our family's needs. So appreciated! Highly recommend!

The Pool House: Hot Tub + Pool + 15 mins downtown
An absolutely perfect weekend at a beautiful home and property. Exceeded our expectations. We will definitely be back! Thank you!

Blue House and a Pool
Lois is such a wonderful and accommodating host! She is quick to respond, extremely generous, and truly cares about the quality of her guest’s stay. The house and property are pristinely kept and there is no shortage of things to do both in and outside of the home. We fished, kayaked, played ping pong and pool, and enjoyed days by the pool and evenings in the new hot tub! I would highly recommend booking Lois’ place if you’re considering a stay at Lake Anna!

Farmhouse on Working Vineyard
The farmhouse was amazing for our all of our extended family celebrating our daughter’s UVA graduation. Tons of room in the cool historic house. Pool among the vineyards was spectacular (as was the wine!). Susan and Tim were great hosts - responsive and helpful. We would HIGHLY recommend the beautiful, peaceful spot for any group gathering.

Stone Spring - Heated Salt Pool - on 2.5 Acres
Great place for a larger group!

Wintergreen Condo~ 1 Minute To Four Seasons Resort
Great location next to slopes and restaurants! Easy to get to, park out front and easy access to enter. Cozy and comfortable inside and everything available we would need for the weekend. Appreciated the plentiful firewood right out front. We enjoyed our stay and hope to be back in the summer! Thank you for sharing your mountain condo with our family!
Condo rentals with a pool

The Modern Mountain Condo
Absolutely wonderful stay! The place was clean, cozy, and very well-kept. The host was kind, welcoming, and made the entire process smooth and stress-free. We felt right at home from the moment we arrived. Would definitely recommend to anyone looking for a peaceful and pleasant getaway. Thank you for a great experience!

Five Minute Walk to Everything!
This place was great! Conveniently located with tons of things to do, many walkable from the condo. The photos and descriptions were super accurate and our dogs even felt welcomed! We appreciated the convenience of The Market, The Edge, Upper Crust, and really enjoyed all of the Memorial Day activities that Dave ad Paige let us know were happening. It was the perfect place to unwind after a day of adventuring. Dave and Paige were super hosts all the way around. We'd love to come back here again!

Eight Minute Walk to Everything
beautiful mountain top and away from the hustle and bustle. The place was very clean and peaceful, but the oven temp was a little off other then taht the place was perfect.

Massanutten Woodstone 2-BR, 2 Bath
Andy was very responsive and gave clear instructions. We had been at this resort a few times in the past and the unit we received was very nicely appointed and updated. We had all amenities and were super close to the indoor pool and gym. Comfortable.

New Construction! 1 Bed/2 Bath, pet friendly
We really enjoyed our stay at your condo. It was nice to be in a newer unit. It was very clean and comfortable. The location is great being walkable to Fire and Frost, a coffee/wood fired pizza restaurant, and we prefer the upper mountain location also being walkable to golf, tennis and trails. We hope to come back to Wintergreen soon. It is a great place to relax!

Tips Up: Cozy Slopeside Retreat w/ Fireplace
Easy check in and access to thr lodge, restaurants, and the market.

Ski-in/Ski-out Wintergreen Highlands Condo -Views!
Lindsay’s place was perfect for our family’s ski weekend. The condo was spacious and had everything we needed. The views were amazing! Lindsay was a great communicator and very responsive host. Highly recommend!

Cozy, clean, quiet mountain condo- King bed
Our stay was lovely! Also, Ritta answered all of our questions in a timely manner. This was our first time using Air BNB, so we had a lot of questions. :)
Quick stats about vacation rentals with a pool in Charlottesville
Total rentals
40 properties
Nightly prices starting at
$314 HKD before taxes and fees
Total number of reviews
910 reviews
Family-friendly rentals
10 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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- Massanutten Resort
- Luray Caverns
- Ash Lawn-Highland
- Early Mountain Winery
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- Lake Anna State Park
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