Charlottesville is a paradise for a history buff! The hometown of no less than three US presidents, the city played an important role in the American Civil War. It is also a significant city rich in African-American history. The city has many historic sites worth visiting such as the historic Downtown Mall and the Fralin Museum of Art at the University of Virginia. If outdoor activities interest you, there are several hiking trails and camping sites close to the city including those within Shenandoah National Park nearby. To explore Charlottesville and its surroundings you will definitely need to plan an extended stay and a relaxing accommodation that will help you rejuvenate quickly. And when it comes to offering a quick rejuvenation, could there be anything better than a refreshing dip in a pristine swimming pool? Read on to discover the top Airbnbs with pool in and around Charlottesville, Virginia.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to pool. The image galleries get refreshed with the latest updates regularly. They were last updated on April 24, 2025.
1. Modern home in a historic neighbourhood
This contemporary house is located in Woolen Mills Retreat close to the Rivanna River. A 75-foot-long (22.86-meter-long) saltwater pool adorns the private yard, which also has an open deck with outdoor furniture. The pool is open from mid-April to September, depending on the weather.
The house has two levels and the interiors have a sleek, modern look. There is an indoor fireplace, a dedicated workspace and a well-equipped kitchen. The upper level has a spacious terrace that overlooks the pool and has views on all three sides.
Charlottesville, Virginia, United States
1.79 km (1.2 mi) from MonticelloSuperhost
Accommodates: 6
Top guest reviews
Location:
the location was good as well close to downtownexcellent location very stylish ample spacethe location of the house was the best part of our stayan easy walk or short ride to local restaurantslocation is very convenient to downtown so getting around was really easyCleanliness:
clean stylish and relatively quietamazingly well decorated and very cleanthe house is beautiful and clean and it felt very privatefresh linens and towels equipped kitchen and cleanliness all true to the property listinghome was clean well-equipped and stylishRead more reviewsAmenities & Room:
design of the space is beautiful we loved the pool and the fully-stocked kitchenthe beds are a tad uncomfortable but not terriblekitchen is very well stocked and the upper level terrace was a real treat
2. Charming apartment ideal for couples (from USD 365)
This single-bedroom apartment is a great place for couples. Attached to a historic house this vacation home has a shared private pool that is open to guests in the summer. The garden view adds a touch of romance to a peaceful and quiet stay.
The air-conditioned unit also has a washing machine and dryer, a TV, toiletries and fast WiFi. For entertainment, Downtown Mall is a 10-minute walk away, so you have access to restaurants and shops. The University of Virginia campus is a short drive away.
Top guest reviews
Host:
owner provided very clear directions and was responsive to questionshost is responsive and responds quicklygarret is such a wonderful host and the family is super welcoming and helpfulgood communication from ownermany thanks to minor garrett and family for the friendly warm welcome to your phenomenal aptLocation:
great location within a 10 minute walk of down townvery easy walk to downtownthe location is within walking distance to downtown with all the wonderful restaurantsgreat spot in a quiet neighborhood close to downtownvery nice rental in great locationCleanliness:
clean beautiful and very quiet neighborhoodthe rooms are clean and a nice sizethis was an excellent place to stay for a long weekend in charlottesville the apartment was beautiful and cleanit was beautiful and clean and would definitely come backclean close to everythingRead more reviewsAmenities & Room:
amazing tv with every channel imaginable (and complimentary netflix) very quiet space and private on a gorgeous propertywonderful books to read here as well as multiple channels to view on the tv
3. Snug studio apartment with a shared pool (from USD 207)
This cosy studio apartment has space for two guests and is only 0.80 kilometres (0.50 miles) away from Downtown Mall and Main Street. The apartment’s proximity to shopping areas means there is access to restaurants, shops, breweries and enough entertainment to keep you occupied.
After a day in town, you can come back to this comfortable home and take a dip in the pool or lounge in the chairs in the yard. The pool is a shared space with the owners, who live in the main house on the property. The home also has an outdoor deck on the upper level where you can enjoy some beautiful sunrises.
Top guest reviews
Host:
the hosts are lovely and made me feel very much at homerobyn is a great host who gives you all the privacy you could wantrobyn was a great host and responded very quickly to any questionswonderful cozy and private space with beautiful grounds and helpful hostsrobyn and her wife stacey were gracious hostsLocation:
great location within walking distance to muchgreat location and lovely placeperfect location for up to two visitorsgreat space and great locationit was an easy walk to the main strip with wonderful restaurantsCleanliness:
everything was very clean and newapartment was very clean and had everything we neededclean and comfortable it has everything you needawesome location cute space clean and easy communicationthe apartment is very comfortable and cleanRead more reviewsAmenities & Room:
fabulous well equipped kitchen and all amenities coveredbeautiful pool views were a bonus thanks robyn for hosting usthe shower is wonderful which is a rare find at most air b & bsfantastic place and comfortable place in a cottage apartment behind a beautifully renovated propertyto be honest i went for the pool and it didn't disappoint
Nearby Airbnbs with pool
4. Historic farmhouse from the 1800s (from USD 531)
If you are looking for accommodation that places you close to nature, this cottage from the early 1800s is the perfect place. Just 12 minutes away from Charlottesville, it is also a UNESCO World Heritage site and was formerly owned by Thomas Jefferson. It is located on a farm and has numerous outdoor activities such as watching wildlife, hiking the trails on the property and kayaking.
Sunny days are best spent at the outdoor saltwater pool complex with showers and a changing area open for guests to use. The complex also houses private hot tubs for each unit.
Top guest reviews
Host:
steven is a great hoststeven was a very welcoming and caring hoststeven is a great host… helpful and friendlyhe is a great hoststeven was very accomodating to some of our last minute logistical changes and was a great hostLocation:
this place was absolutely perfect we couldn’t have asked for better accommodations or locationwill recommend this place to my friendsCleanliness:
the interior of the house was extremely clean and pleasantly furnishedRead more reviewsAmenities & Room:
the pool and the deck are spacious and overlook a beautiful sunset viewthe cottage itself was cozy and perfect for just the 2 of usour favorite thing was relaxing in the cabana by the pool with that gorgeous viewthis property offers the perfect backyard setting from the hammocks to the swimming poolthe pool and resting areas by the pool were extremely comfortable
5. Luxurious house with private pool and lake (from USD 734)
This house is set on 15 acres (6.07 hectares) of land in the midst of nature, with a private lake surrounded by lush green woods. The picturesque setting makes it perfect for small weddings, which the owner allows. A private outdoor heated saltwater pool and a private hot tub on the outdoor deck complete the serene picture. The pool is open from mid-April to October and the temperature is set at 26.6 °C (80 °F).
The five bedrooms and spacious common areas are capable of accommodating large groups of people. A pool table, Bluetooth sound system and a ping-pong table are other amenities that are bound to make family nights fun.
Top guest reviews
Host:
the host was wonderful and responded very quicklyour hosts were very helpful very communicative and responsive to any questions we hadseth and carla were great hosts once again this is the second time we have rented this homeincredibly responsive if anything comes upcarla was our host and she communicated well and made sure we were comfortableLocation:
great house great backyard great locationthis was the ideal place for our christmas gatheringgreat place to stay close to so many fun places to visitloved the hot tub and proximity to walks on quiet roadsideal location we were in the middle of the wineries spa and downtown charlottesvilleCleanliness:
the large pool was clean and area was beautifully landscapedthe house was very clean and had everything we needed for a fun weekendthe house was beautiful spacious and very cleanthe place was very clean and the kitchen is an absolute dreamspacious exceptionally maintained and extremely well furnishedRead more reviewsAmenities & Room:
the house was plenty big with the perfect amenities we especially loved the poolthe pool was great with awesome views of the lake that's on the propertythe house is an excellent place for a large group very comfortable and lots of great amenitiesplenty of areas to relax and enjoy the pool was amazing and the view from the poolwe fit everyone easily and enjoyed the massive well-equipped kitchen for family-style meals
6. Milton Cottage (from USD 479)
This cosy cottage sits on 12 acres (4.86 hectares) of land in the countryside. The property has a 60-foot (18.29-metre) lap pool shared with the owners, who live in a house next to the cottage. The fenced-off pool is surrounded by flowering hedges and offers magnificent views. You can relax in the deck loungers as well.
Fit for a couple, other amenities include an outdoor patio, a fire pit, a grill and barbecue utensils. Attractions such as Downtown Mall and Monticello are within 17 minutes of driving distance.
Top guest reviews
Host:
he was very responsive to any questions we hadhosts were very friendly and helpfulgordon was a great host and everything was just as describedgordon was really helpful and friendlygordon is very responsive and hospitableLocation:
best possible location in charlottesvillethe location is wonderful not far from downtown charlottesville and close to many winerieswould definitely stay at this location againlocation was great and we'd definitely stay againreally cute place super clean and an easy check inCleanliness:
clean private and charmingthe space was clean and comfortableextremely private and very clean as wellit was very private clean and cozywell appointed clean and very eco-friendlyRead more reviewsAmenities & Room:
the birds and butterflies around the pool are stunning lots of deer watchingthe pool is a huge bonus as well as the covered porch to sit and watch the sunsets
7. Barn studio fit for two outside Charlottesville (from USD 227)
With a gorgeous view of the rolling hills, this unique barn studio lies outside the hustle and bustle of Charlottesville. The property has an outdoor pool that is open to the skies. The pool is open till 6.30pm, but if you would like for it to be open for longer, you can request to do so.
You can enjoy a romantic evening by the fire pit and enjoy the rolling panoramic views on the property. There are wineries and walking trails in the vicinity and Charlottesville is just a 15-minute drive away.
Top guest reviews
Host:
trish & her hubby were excellent hoststrish is a great host and made sure we felt welcome and free to make ourselves at hometrish was a wonderful hosttrish is a very thoughtful hosttrish was an exceptional host and very communicative and helpfulLocation:
the location was perfectbeautiful airbnb in a pretty locationperfect location for sight seeing dining adventuring etcthe location was perfect and convenient to everything in and around charlottesvillewe loved our stay it’s a wonderful place and a great locationCleanliness:
everything was clean tidy and thoughtfulclean the pool was wonderful a perfect weekend getawayeverything was very clean and ready for us at check-incottage was clean and had everything we neededclean cute comfortable serene and the perfect getaway for a few days in charlottesvilleRead more reviewsAmenities & Room:
the furniture and bed are super comfortable and the setting is quiet and serenewe will definitely return to enjoy your new fire pit (complete with fixin's for s'mores ) and lovely poolthe studio was very clean and comfortable with a beautiful view from the balconygorgeous view from the porch and bed is super cozy we slept greatgreat location amazing views and loved the pool we had everything we needed and were very comfortable
8. Mountain retreat with a private pool
A stunning view of the Blue Ridge Mountains is reason enough to consider booking this mountain retreat. It is located on 18 acres (7.28 hectares) of land in the midst of woods and is just a 15-minute drive from Charlottesville. Ideal for large groups, it has a full kitchen, fireplace and spacious exterior.
The outdoor patio is a great area for the groups to spend evenings by the fire pit and sunny days swimming in the pool or soaking in the hot tub. The pool area is due to open on Memorial day weekend and is open from 8.00am to 10.00pm. It is a private pool only for the guests and is gated and has child-safety latches to maximise safety.
Charlottesville, Virginia, United States
15.14 km (9.5 mi) from MonticelloAccommodates: 8
Top guest reviews
Host:
he was very responsive to any questions or requestsengin was the perfect hostand the host is very responsive kind and accommodatingengin is a great host highly recommendedengin was very kind gave us great recommendations and answered any questions we hadLocation:
beautiful place in a great locationthe location is superb private yet convenient to charlottesville and the universitygreat spot if you want to feel the woods but still be close to towngreat place would have been even better in the summer when we had pool accessCleanliness:
really clean and nice placethe house was extremely clean and spaciousit was very clean fully stocked with dishes and cooking tools the beds were very comfortablethe beds were high quality clean and had great pillowsthe house was so clean and tastefully decoratedRead more reviewsAmenities & Room:
the pool and view are fantasticthe pool hot tub and patio are heavenlythe outdoor patio and pool were our favoritesand the beds were super comfythe outdoor setup and amenities (pool hot tub fire pit) are wonderful
9. Lavish estate close to Charlottesville (from USD 4900)
A 70-year-old home on 17 acres (6.88 hectares) of land, this property is on the banks of the Rivanna river and is an absolute dream. The home receives lots of natural light and offers glorious green views of the outdoors. There is also a dedicated workout room with equipment and a media room.
With grounds like these, outdoors is the place to be. You can head down to the waterfront which has a private deck. Or use the kayaks and paddle boards for a fun time in the water. Apart from the indoor kitchen, the property has a stunning outdoor kitchen perfect for cookouts located by the poolside. The 40-foot (12.19-meter) private pool and adjacent hot tub are great places for the groups to spend time together.
Top guest reviews
Host:
beautiful home and property we enjoyed our stay and the hosts were very communicativerobin's place was perfect she was very helpful with recommendations and planning our tripgreat house perfect for our weekend and robin was the best hostCleanliness:
this is a great location the home is well appointed and everything is clean and well maintainedRead more reviewsAmenities & Room:
the house was perfect for multiple families incredible pool and outdoor space
10. Secluded mansion by the lake
This lakeside home in Keswick is a tranquil and peaceful accommodation with plenty of amenities such as a full kitchen, a game room and a gym. You can enjoy walking around the property or kicking back in the hammock outdoors.
The fenced-off outdoor saltwater pool is the centre of all activity. With multiple options for outdoor seating, deck loungers, a daybed, a hot tub and a grill, you can spend the entire day relaxing and sunbathing under the clear blue sky. There are pool toys provided as well so children can enjoy themselves thoroughly. The waterfront deck has kayaks and paddleboards for guests’ use on the water.
Keswick, Virginia, United States
11.29 km (7.1 mi) from MonticelloAccommodates: 8
Top guest reviews
Host:
kate is a very responsive hostkate was a great host and she went beyond to make our stay comfortable and enjoyablekate and jeremy are super hosts and very responsivewonderful stay - lovely pool house and very kind and responsive hostCleanliness:
kate's guesthouse was very beautiful and cleanRead more reviewsAmenities & Room:
we really enjoyed our long weekend getaway relaxing by the private pool with a beautiful view
Travel at your own pace in Charlottesville
Charlottesville is a destination that is best visited leisurely. Apart from doing justice to the informative historic sites, you should definitely immerse yourself in the surrounding countryside with its walking trails, wineries and outdoor activities. Comfortable accommodation with a pool will definitely upgrade your experience of Charlottesville. Be sure to pick a vacation home from the list above for an enjoyable stay.
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