Holiday 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

Guest favourite
Home in Massanutten
4.88 out of 5 average rating, 119 reviews

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

KimRating, 5 stars3 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 favourite
Home in Boston
4.96 out of 5 average rating, 141 reviews

Peacefield - Blue Ridge views near Culpeper

AlanRating, 5 stars4 weeks ago
3 Nights was not enough for our 7 member family. We cooked, grilled, soaked in the hot and best of all had a delightful tour of Barbara's and Mike's Sheep Farm, all fit in around wedding events in Rixeyville. If life wouldn't have been in the way, 2 more days enjoying the massive deck and game room downstairs would have been perfection.
Guest favourite
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 favourite
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 favourite
Home in McGaheysville
5 out of 5 average rating, 70 reviews

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

JuliaRating, 5 stars3 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 favourite
Home in Nellysford
5 out of 5 average rating, 27 reviews

Foxy Retreat Stoney Creek/ Wintergreen Golf/ Ski

CarlyRating, 5 stars1 day ago
We had a great time at the foxy retreat this past weekend! The house is adorable and has so much space. The backyard feels so private and was such a fun place to hang out. Tammy was a great host, and gave us all the information we needed!
Top guest favourite
Home in Charlottesville
4.97 out of 5 average rating, 64 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!
Guest favourite
Home in McGaheysville
5 out of 5 average rating, 8 reviews

FREE Summer POOL PASS, PoolTable-Outdoor Fire-PS5

DannyRating, 5 stars4 weeks ago
Great house. It was able to accommodate our family of 9. Close distance to all the attractions in Massenutten. We would definitely book again

Apartment rentals with a pool

Guest favourite
Apartment in Wintergreen Resort
4.94 out of 5 average rating, 218 reviews

The Modern Mountain Condo

KileyRating, 5 stars1 week 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 favourite
Apartment in Wintergreen Resort
4.96 out of 5 average rating, 292 reviews

Five Minute Walk to Everything!

KatieRating, 5 stars1 day ago
Perfect in every way. The location did not disappoint and my small dogs felt right at home. Many thanks—we will be back!!
Top guest favourite
Apartment in Wintergreen Resort
4.97 out of 5 average rating, 105 reviews

Panoramic Mountain View~ Wintergreen~ Ground Level

TrenaRating, 5 stars3 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 favourite
Apartment 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 favourite
Apartment in Wintergreen Resort
4.91 out of 5 average rating, 166 reviews

Tips Up: Cozy Slopeside Retreat w/ Fireplace

DennisRating, 5 stars6 days ago
Cute 1 bedroom condo on top of the mountain at a ski resort. Would deff book again if looking for a place in area.
Guest favourite
Apartment 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 favourite
Apartment in Wintergreen Resort
4.98 out of 5 average rating, 134 reviews

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

LaurenRating, 5 stars1 day ago
Mary’s place was exactly what we needed for our family with small children. The kids loved eating on the deck and being able to sleep in the same room but in their own bed. They had games available and everything was nice and clean. Mary was also quick to respond with any questions we had. We would definitely stay here again!
Guest favourite
Apartment in Charlottesville
4.86 out of 5 average rating, 130 reviews

Perfect Spot in Charlottesville

RachelRating, 5 stars4 months ago
I have absolutely no reservations recommending Angelique’s Airbnb. We had a terrific two months stay here, Angelique is very responsive, property is as described. It has comfortable beds and living room and even walkable to the closest shopping area. Highly recommend staying here if you are looking for a place in Charlottesville

Quick stats about holiday rentals with a pool in Charlottesville

  • Total rentals

    40 properties

  • Nightly prices starting at

    £30 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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