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

Guest favorite
Home in Charlottesville
5 out of 5 average rating, 11 reviews

3Bdrm | Hot tub, Firepit, Wineries | 9miles to UVA

MaryRating, 5 stars3 months ago
What a gorgeous spot! 20 minutes from UVA, you’re right down the road from Monticello in beautiful wine country. The house is sparkling clean with all the amenities you could possibly need. The kitchen is HUGE, and the open floor plan really makes for a fun weekend with friends/family. We had a much needed Mom’s weekend, and really enjoyed sitting in the hot tub and taking in the woods around us. Jason was very helpful and friendly in his communication, we would definitely love to come back.
Guest favorite
Home in Boston
4.96 out of 5 average rating, 145 reviews

Peacefield - Blue Ridge views near Culpeper

CurtRating, 5 stars1 week ago
The Airbnb advertisement for the house does not adequately convey how nice this place actually is! Most of the items in the house: furniture, appliances, cookware, grill, bedding, towels, etc. are of high quality and excellent condition. The interior of the house is open, spacious and beautiful. It has high ceilings in most rooms, and a vaulted ceiling over the kitchen, dining room, family room, living room, and foyer. Barbara and Mike gave our girls a tour of the sheep farm and let them meet their dog. They were also responsive quick to take action whenever we had issues (like tripping a circuit breaker and running out of propane). For an additional charge of $75, they warmed up the pool for me twice because I am not a fan of water temps in the low 80s. The location is beautiful and secluded, but you can get to Shenandoah hiking trails in 20-30 minutes or Walmart/Safeway in 15 minutes. We loved our time here and would definitely stay at Peacefield again.
Top guest favorite
Home in Wintergreen Resort
4.88 out of 5 average rating, 136 reviews

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

KatieRating, 5 stars3 months ago
We had the absolute best time staying here. We had two families staying together, 10 total. With more than enough space! The location was perfect. The space was clean and cozy. We had the best time and made some amazing memories with our friends. Also we slept at night on the third floor with a window opened and it was so quiet outside! Thank you for opening your home to us!
Guest favorite
Home in Afton
4.94 out of 5 average rating, 145 reviews

Farmhouse on Working Vineyard

SarahRating, 5 stars3 weeks ago
We stayed here for a bachelorette weekend and had a great time. The house was even bigger and cozier than I anticipated and the views were gorgeous. We loved being on the same property as Cardinal Point Winery and walked down to do a tasting/enjoy some bottles. The kitchen was stocked with all the tools we could have needed and the pool area was great!
Superhost
Home in Town of Rockingham
4.79 out of 5 average rating, 262 reviews

Stone Spring - Heated Salt Pool - on 2.5 Acres

MollyRating, 5 stars2 weeks ago
We had a wonderful getaway at Seths place in Rockingham. Perfect location for a group of 12 girlfriends that wanted to relax. Loved the pool and the porch/patio! Felt like Tuscany. Seth and Carla were extremely responsive to the couple of small issues we had. Definitely recommend.
Guest favorite
Home in Wintergreen Resort
4.96 out of 5 average rating, 106 reviews

Peaceful 3-BR Mountain home w/Fireplace + Hot tub

NikiRating, 5 stars2 months ago
Our family of four needed a quiet get away, and we enjoyed the beautiful days and evenings, inside and on the deck! Hikes nearby, spa nearby, restaurants, grocery, gas also nearby. Great resort year round! Lots of activities if you want them, and lots of peaceful nature if you want. Great!
Top guest favorite
Home in Wintergreen Resort
4.97 out of 5 average rating, 115 reviews

Bear's Mountain Escape

LauraRating, 5 stars2 weeks ago
Great stay! Perfect location and space was great. A tad smaller than what it looked like in the photos, but overall, great! The kitchen did not have any pantry space, but we made do with a shelf above the microwave and bins on top of the fridge. A day prior to check-in, I received an email stating the pool in the complex was closed for repairs. A bit disappointed at first, but it ended up working out really well. We had access to the SPA indoor and outdoor pools and the outdoors ended up being too cold to swim in. The indoor pool was no problem at all and they were very accommodating with lettings us have access throughout our stay. We would stay here again for sure!
Top guest favorite
Home in Massanutten
5 out of 5 average rating, 19 reviews

New build, Indoor Pool, hot tub, home theater, 5BR

JoyRating, 5 stars3 days ago
Amazing! We rented this for our annual extended family vacation and everyone agreed this was the best AirBnB we've stayed at on these trips. Jonah and Fern were so kind and responsive in all their communications, the house manual had everything we needed, and the home itself was beautiful, clean, and fun. Plenty of bedrooms and bathrooms, the best-stocked kitchen we've had at a rental, lots of nice amenities (pool, theatre, hot tub, etc), and a very peaceful neighborhood. We'd love to stay again and would recommend Splash at the Slopes to anyone traveling to the area in any season. Thank you for a lovely and memorable trip for our family!

Condo rentals with a pool

Guest favorite
Condo in Wintergreen Resort
4.93 out of 5 average rating, 224 reviews

The Modern Mountain Condo

CharlesRating, 5 stars1 week ago
My friends stayed here through from the 14th to the 16th of June for a bachelor party. When we first walked in, we were so excited to see that the condo lined up to our expectations and even went on to exceed them. Even in the summertime, Wintergreen and the surrounding areas offered much to do recreationally. Keith's wonderful condo acted as a terrific focal hub for us on our excursions down the mountain. Keith was so helpful and responsive throughout our entire stay, and was quite flexible on accommodating an early check-in after our earlier camping experience ended up with us sleeping in my car from rain. He also answered each one of my questions and was extremely knowledgeable as to the community policies, especially when it came to parking. The check-out instructions were easy to follow and very accommodating of our time. We had an extremely wonderful stay at their condo, and I am even considering re-booking it for myself later on in the year! You truly won't find better hosts.
Guest favorite
Condo in Wintergreen Resort
4.96 out of 5 average rating, 134 reviews

Mtn/Firework Views from Private Deck ~ King Suite

JenniferRating, 5 stars2 weeks ago
Susie’s place was PERFECT for my weekend of solitude and peace. I was able to relax and just take it easy in a comfortable home with a beautiful view. The home was clean and felt so comfortable. There were lots of personal touches that really show Susie put a lot of thought into the space. For example, the motion sensor nightlights in the bathrooms. And the dimmable lights in the bedroom. Check in and check out instructions were very clear and easy to follow, she even included a map of where to park! I can’t say enough great things about this experience.
Top guest favorite
Condo in Wintergreen Resort
4.95 out of 5 average rating, 296 reviews

Five Minute Walk to Everything!

CarolynRating, 5 stars4 weeks 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 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, 208 reviews

New Construction! 1 Bed/2 Bath, pet friendly

SusieRating, 5 stars1 month 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, 176 reviews

Tips Up: Cozy Slopeside Retreat w/ Fireplace

BrianRating, 5 stars3 weeks ago
Nice home, in an ideal location. Great communication and quick to respond as needed. Recommend the home and location!
Guest favorite
Condo in Wintergreen Resort
4.96 out of 5 average rating, 181 reviews

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

JeffRating, 5 stars3 weeks ago
Fantastic place to stay and a very good host. Communication from the host was always extremely fast, detailed, and helpful. The space itself is fantastic - perfect view of the Blue Ridge Mountains skyline and sunset. Also, especially in the skiing off-season (which it was for our visit), it’s very close to Devil’s Backbone, Bold Rock, Three Notch’d, etc, but you are still far enough away to feel like you’ve gotten away from everything. There’s also a solid-looking pizza restaurant in walking distance, though we did not make it there during our visit. The condo has 2 stories that both serve their purpose very nicely - the upstairs has a nice living space and a clean, very usable kitchen. The downstairs has bunk beds and you could walk from the downstairs patio to the slopes. In the offseason, there is a nice hiking trail that is no more than 100 yards away. Overall, we had a blast and would love to return! Thank you!
Top guest favorite
Condo in Wintergreen Resort
4.94 out of 5 average rating, 251 reviews

Cozy, clean, quiet mountain condo- King bed

ChelseaRating, 5 starstoday
John and Ritta were amazing to work with and so helpful. We found their cozy condo after a trip fell through. We were so glad to have found this amazing place in close proximity to hiking spots, good food, wineries and breweries. We will definitely be back.

Quick stats about vacation rentals with a pool in Charlottesville

  • Total rentals

    40 properties

  • Nightly prices starting at

    G$8,368 GYD 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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