Vacation rentals with a pool in Charlottesville

Find and book unique homes with a pool on Airbnb

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Popular amenities for Charlottesville rentals with a pool

House rentals with a pool

Superhost
Home in Ruckersville
4.75 out of 5 average rating, 20 reviews

Kismet Cottage | Cville Home with Pool & Mtn Views

LindsayRating, 5 stars23 months ago
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.
Guest favorite
Home in Massanutten
4.88 out of 5 average rating, 119 reviews

Mid-Century Modern: Hot Tub~Free Pool Access~Grill

KimRating, 5 stars5 months ago
Great mountain house! House was clean and had everything we needed. The host sent us local recommendations and checkin/out was easy!
Guest favorite
Home in Boston
4.96 out of 5 average rating, 143 reviews

Peacefield - Blue Ridge views near Culpeper

ClaudiaRating, 5 stars3 weeks ago
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!
Guest favorite
Home in Swoope
5 out of 5 average rating, 37 reviews

The Pool House: Hot Tub + Pool + 15 mins downtown

ErinRating, 5 stars8 months ago
An absolutely perfect weekend at a beautiful home and property. Exceeded our expectations. We will definitely be back! Thank you!
Guest favorite
Home in Mineral
4.86 out of 5 average rating, 29 reviews

Blue House and a Pool

ErinRating, 5 stars3 weeks ago
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!
Guest favorite
Home in Afton
4.94 out of 5 average rating, 143 reviews

Farmhouse on Working Vineyard

BartRating, 5 stars2 weeks ago
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.
Superhost
Home in Town of Rockingham
4.79 out of 5 average rating, 261 reviews

Stone Spring - Heated Salt Pool - on 2.5 Acres

Clinton JohnRating, 5 stars1 month ago
Great place for a larger group!
Top guest favorite
Home in Wintergreen Resort
4.93 out of 5 average rating, 58 reviews

Wintergreen Condo~ 1 Minute To Four Seasons Resort

KristenRating, 5 stars3 months ago
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

Guest favorite
Condo in Wintergreen Resort
4.93 out of 5 average rating, 221 reviews

The Modern Mountain Condo

PratikRating, 5 stars1 week ago
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!
Top guest favorite
Condo in Wintergreen Resort
4.96 out of 5 average rating, 294 reviews

Five Minute Walk to Everything!

CarolynRating, 5 stars1 week ago
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!
Guest favorite
Condo in Wintergreen Resort
4.94 out of 5 average rating, 229 reviews

Eight Minute Walk to Everything

SarahRating, 5 stars4 weeks ago
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.
Guest favorite
Condo in McGaheysville
4.84 out of 5 average rating, 144 reviews

Massanutten Woodstone 2-BR, 2 Bath

OsvaldoRating, 5 stars5 months ago
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.
Guest favorite
Condo in Wintergreen Resort
4.95 out of 5 average rating, 207 reviews

New Construction! 1 Bed/2 Bath, pet friendly

SusieRating, 5 stars2 weeks ago
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!
Guest favorite
Condo in Wintergreen Resort
4.91 out of 5 average rating, 175 reviews

Tips Up: Cozy Slopeside Retreat w/ Fireplace

PhillipRating, 5 stars1 week ago
Easy check in and access to thr lodge, restaurants, and the market.
Guest favorite
Condo in Wintergreen Resort
4.96 out of 5 average rating, 178 reviews

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

TimRating, 5 stars2 months ago
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!
Top guest favorite
Condo in Wintergreen Resort
4.94 out of 5 average rating, 249 reviews

Cozy, clean, quiet mountain condo- King bed

LisaRating, 5 stars2 weeks ago
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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