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

Top guest favorite
Home in Boston
4.96 out of 5 average rating, 140 reviews

Peacefield - Blue Ridge views near Culpeper

ErnieRating, 5 stars1 month ago
We had a wonderful time in this great house! The house was big with everything you could ask for. Our daughter was getting married at Rock Hill farm which is only 3.5 miles away and the house provided us a quiet, peaceful place to come home to after a busy day and evening. There were sheep grazing beside the house! We didn’t get a chance to tryout the spa and pool, but maybe next time. We highly recommend!!!
Top guest favorite
Home in Nellysford
5 out of 5 average rating, 70 reviews

Spacious retreat: Game Room+Hot Tub in Wintergreen

DianaRating, 5 stars1 week ago
We had an absolute wonderful time in Joanna’s beautiful place. So very clean and everything organized nicely. Game room is fun. The view is gorgeous. I hope to stay her again soon!!! She’s great at what she does!!!!
Guest favorite
Home in Afton
4.94 out of 5 average rating, 141 reviews

Farmhouse on Working Vineyard

KatyRating, 5 stars6 months ago
Susan’s farm house was perfect for enjoying a relaxing getaway with plenty of space for multiple families and kids. All of the spices are very large and honestly it’s better in person than in the pictures. We would recommend it to anyone and return again! The kitchen was nicely stocked with everything you could need. And it was great being right on the winery.
Guest favorite
Home in Massanutten
4.96 out of 5 average rating, 80 reviews

Massanutten Mountain, Hot Tub, FirePit,Pool Table

NeilRating, 5 stars1 week ago
Overall, the listing was exactly as advertised. Debra sent plenty of instructions the week before our stay and they were easy to follow to get in. House was clean and cozy and the beautiful surroundings were exactly what we were looking for! I would definitely recommend this home to anyone looking to stay in the area.
Top guest favorite
Home in McGaheysville
5 out of 5 average rating, 70 reviews

Mt. Mindset-DOG & Family Friendly! Game room!

JuliaRating, 5 stars2 weeks ago
We felt right at home, everything was pristine and clean, peaceful, beautiful tucked away private location. The amenities were everything we needed to have the ease of a getaway where we didn’t have to worry about packing extra items. From baby equipment to the game room we felt like it fit all of our needs perfectly. I appreciated all the thoughtful details that are put in place to make sure you truly are comfortable as a family traveling. Loved the gazebo and firepit on the deck! The ambiance really suited all our guests. Thanks for a wonderful stay!
Top guest favorite
Home in Nellysford
5 out of 5 average rating, 26 reviews

Foxy Retreat Stoney Creek/ Wintergreen Golf/ Ski

ShantinaRating, 5 stars3 days ago
This was an excellent location and very comfortable my entire family ranging from 3 yrs old to big kids age 70😀
Superhost
Home in Shenandoah
4.89 out of 5 average rating, 54 reviews

Pet Friendly, Views, Hot Tub, Firepit, Kayak, BBQ

MelissaRating, 5 stars2 months ago
This house is perfect for a family or group. The house has everything you need. Very comfortable, cozy, and inviting! Views for miles! We would highly recommended this house for a weekend getaway to explore Massenutten (20min) and Luray Caverns (18min). My family made the best memories this weekend.
Top guest favorite
Home in Charlottesville
4.97 out of 5 average rating, 63 reviews

Rivanna Farm Estate South Pickleball I Pool

BrookeRating, 5 stars4 months ago
Our family of four had a wonderful holiday getaway with my mother in law joining from Richmond for Thanksgiving Day. The house was everything we expected it to be and the hosts so kind and thoughtful. I realized I had forgotten a roasting pan for the turkey and instead of having to run out and fight crowds, Larry appeared at our door with one for us to borrow. We loved Marty the Donkey! The house was the perfect spot to relax, get caught up as a family and enjoy each other in a beautiful and peaceful setting. We already loved Charlottesville but love it even more now that we know about this special gem! We will be back!

Condo rentals with a pool

Guest favorite
Condo in Wintergreen Resort
4.94 out of 5 average rating, 217 reviews

The Modern Mountain Condo

KileyRating, 5 stars5 days ago
Had a great stay for a few nights in this condo. Comfortable and clean as a lovely escape while we enjoyed local hikes and breweries. Convenient to the wintergreen market which was helpful for what we may have forgotten or for anything else we wanted. Looooved having the wood burning fireplace too! We’d love to come back.
Top guest favorite
Condo in Wintergreen Resort
4.96 out of 5 average rating, 291 reviews

Five Minute Walk to Everything!

MacieRating, 5 stars3 weeks ago
Was a great place a wonderful clean place loved it so beautiful peaceful and convenient. Will definitely book again
Top guest favorite
Condo in Wintergreen Resort
4.97 out of 5 average rating, 104 reviews

Panoramic Mountain View~ Wintergreen~ Ground Level

TrenaRating, 5 stars2 weeks ago
Excellent stay! Exactly as pictured. Beautiful views and nicely decorated, updated and comfy condo. I’m sure it’s great during ski season but so peaceful and restful in off season. Responsive host. Highly recommend this spot!
Top guest favorite
Condo in Wintergreen Resort
4.96 out of 5 average rating, 205 reviews

New Construction! 1 Bed/2 Bath, pet friendly

AmandaRating, 5 stars1 month ago
Lisa's condo was fabulous! It was decorated beautifully and in a very peaceful location. It was great not having to walk up and down multiple flights of stairs. If you need anything, she is quick to answer. It was the cleanest dog friendly Airbnb that we have ever stayed in!! We have a hypoallergenic dog so I appreciated not being covered in dog hair. We will definitely be staying again in the future! Thank you, Lisa!
Guest favorite
Condo in Wintergreen Resort
4.91 out of 5 average rating, 164 reviews

Tips Up: Cozy Slopeside Retreat w/ Fireplace

MeganRating, 5 stars3 weeks ago
It was a great stay here! It’s in the Wintergreen Resort which was great for hikes with the pups, restaurants within walking distance at the resort, and not too far of a drive to wineries & breweries. Would definitely stay again!
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 stars1 month 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!
Guest favorite
Condo in Wintergreen Resort
4.91 out of 5 average rating, 215 reviews

Light Filled Awe-Inspiring Views from Every Window

MattRating, 5 stars2 months ago
Great place. Beautiful view. Everything you’d need.
Top guest favorite
Condo in Wintergreen Resort
4.98 out of 5 average rating, 133 reviews

2-min drive from hiking/resort, stairs-free

AlexisRating, 5 stars5 days ago
We had the pleasure staying here for 3 nights. The condo is beautiful, clean, and in an amazing location. Mary was very responsive and provided wonderful recommendations in the area. I would recommend this lovely place to anyone looking for a getaway at Wintergreen and we will definitely be returning in the future!

Quick stats about vacation rentals with a pool in Charlottesville

  • Total rentals

    40 properties

  • Nightly prices starting at

    $40 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

Destinations to explore