Vacation rentals with a pool in Charlottesville

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Top-rated rentals with a pool in Charlottesville

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Apartment in Madison

4.9 out of 5 average rating, 229 reviews

The Studio at Dark Run Retreat

Quiet studio on a secluded 5 acres only 3 miles from town. Kick back and relax by the pool in the warmer months, or in the hot tub in the cooler months. Small trails lead to the creek running along the property, maybe you'll even catch a glimpse of the deer or turkey that wander thru...we've even seen a lil bear once! There is an apartment above the studio, so we ask that you be mindful of those guests if occupied. *The studio got a make-over! As of 10/6/20, we will no longer be hosting pets*

Sep 24 – Oct 1

€ 90 per night

Superhost

Farm stay in Charlottesville

4.89 out of 5 average rating, 114 reviews

Jefferson Cottage quiet farm close to everything

The cottage circa 1802 offer a peaceful private setting on a historic horse farm once part of Monticello with close proximity to wineries (10 minutes), town (12 minutes), Rivanna River borders the property, Carter mountain (8 minutes) and many other activities. A "Jimmy Buffet" salt water pool complex has a private Jacuzzi for each unit, double bars, two fire pits, frig ,full bath/shower/changing room) There is a private lake (catch and release fishing) and many places to walk on the property.

Feb 21 – 28

€ 269 per night

Guest favorite

Farm stay in Stanardsville

4.96 out of 5 average rating, 511 reviews

GreeneHouse.POOL*HotTub*MTNviews*FarmGOATS*Hiking

The private, adults 18+only, Greene House apartment is located at ground level of the main farmhouse. Views out the kitchen windows and private patio overlook the piedmont valley. Great for couples or a gathering of 4 adult friends. Private hot tub on porch+shared in-ground pool. A ten minute hike gets you into Shenandoah National Park Back Country. 20 min. to Swift Run Gap SNP. Walking trails. No pets. Check out Cair Paravel Farmstead on FB/the web to see all we have to offer. High speed WiFi

Feb 15 – 22

€ 166 per night

Guest favorite

Guesthouse in Afton

5.0 out of 5 average rating, 223 reviews

Mountain Cottage / Pool, heart of 151 Brew Trail

Wake to gorgeous Mountain views and our rolling green meadows bordering the Rockfish River on our family estate. Private attached unit with an inground pool (mid April-mid Sept.) in the Blue Ridge mountains of Nelson County Virginia centered on the 151 Brew Ridge Trail. Much preparation has gone into making your stay beautiful, convenient and comfortable. No need to physically interact if that is your desire. Enjoy swimming, hiking, kayaking, horse back riding, skiing, snowboarding, and more!

Jun 7 – 14

€ 305 per night

Guest favorite

Cabin in Gordonsville

4.82 out of 5 average rating, 226 reviews

1700's Summer Kitchen Cottage #147 Pool & WIFI

Escape from city life on a beautiful historic 250-acre estate. It is close to historic attractions and wineries. You’ll love it because of the gorgeous outdoors and historic charm. This place is good for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets). There is WIFI. This is only 20 minutes away from Jefferson's Monticello, and James Madison's "Montpelier" or play golf (5 min) away. Treat yourself to an onsite certified massage wellness therapist.

Aug 17 – 24

€ 154 per night

Guest favorite

Guesthouse in Charlottesville

5.0 out of 5 average rating, 110 reviews

Hidden Gem near town and Monticello with a pool

We call this our hidden gem because it's not too far from town, wineries, UVA, Monticello and more that Charlottesville has to offer, but yet it's far enough away from the hustle and bustle. The renowned Clifton Inn, a popular destination wedding venue is less that 1/4 mile away. Thomas Jefferson's Monticello is a 7 minute drive. The campus of UVA is a 15 minute drive. We call this our studio loft because it has the feel of a mountain cabin. The views are gorgeous and the setting is peaceful.

Nov 24 – Dec 1

€ 206 per night

Guest favorite

Condo in Wintergreen Resort

4.95 out of 5 average rating, 199 reviews

Eight Minute Walk to Everything

This one-bedroom, one-bath condo is centrally located. Ski check-in, restaurants, the mountaintop provisions market, and the Mountain Inn and conference center are all within an 8 minute walk. It's a one-story, downstairs unit that includes a back porch with just a few steps down to the ground. Perfect for taking the dog outside in the pet-friendly space. Full kitchen and dishes, wood-burning fireplace, balcony, and all towels and linens are provided for your convenience. Sleeps 3.

Aug 3 – 10

€ 121 per night

Guest favorite

Guesthouse in Troy

4.99 out of 5 average rating, 118 reviews

Beaver Pond Farm - Near Charlottesville

Relax at this unique and tranquil getaway. Sit on the screened in porch and enjoy the sights and sounds of nature while you enjoy a beverage. Take a walk on miles of trails that are adjacent to the property. Visit the Downtown Mall, Monticello, a Winery, a Brewery, or UVA (20 min). Enjoy a dip in the pool (JUN-AUG) or relax by the firepit - perhaps joined by the horses for cocktails. Feel like staying in - SmartTVs and Gig-speed Internet await. Easy checkout. No cleaning fee.

Sep 19 – 26

€ 140 per night

Guest favorite

Farm stay in Barboursville

4.98 out of 5 average rating, 177 reviews

Moonfire Farm cozy Shenandoah Region Getaway

Experience charm and nature at Moonfire Farm! Our finished basement on a 5-acre hobby farm offers delightful animal encounters with chickens, ducks, alpacas, and hilarious goats. Our active family of three, including our 7-year-old daughter Piper, welcomes you. High-speed Internet and nearby wineries, breweries, hiking trails, and pick-your-own fruit locations await you. Explore our guidebook for recommendations. Book now for a memorable farm getaway!

Oct 15 – 22

€ 151 per night

Guest favorite

Home in Charlottesville

4.98 out of 5 average rating, 250 reviews

A Modern Mountain Guesthouse

Our newly renovated guesthouse is located in the prestigious Ivy neighborhood of Charlottesville, Virginia overlooking the stunning Blue Ridge Mountains. We’re within a 15-minute drive to The University of Virginia and downtown Charlottesville and a 20-minute drive to the Nelson 151 winery, brewery, and cideries. We're group (ideal for bachelorette parties) & family friendly and can help you arrange the perfect getaway.

Aug 3 – 10

€ 529 per night

Guest favorite

Farm stay in Crozet

4.95 out of 5 average rating, 154 reviews

Refreshed '24, Mt Views & Pool: Sunset Farm Studio

2024 Upgrades! Sunny, spacious Q bed/living room upstairs (wood stove); mini-kitchen & bath downstairs on a 10-acre farm with 180-degree views of Blue Ridge Mts. A floor mattress is available for an extra fee. Quiet, private, big-sky, 5 min from Crozet. I have a blind dog; no visitor dogs. It is a perfect place to be on retreat/ wine country or get work done (WiFi and a printer). NEW 50" TV.

Sep 20 – 27

€ 156 per night

Guest favorite

Guesthouse in Midland

4.97 out of 5 average rating, 151 reviews

Modern Farm Stay

This studio apartment provides a peaceful farm getaway while still offering lots of local attractions. Convenient to wineries, farm markets, the Flying Circus, and Shenandoah National Park. We are close to several wedding venues (Great Marsh Estate, Morais, and Poplar Springs to name a few) so this is a great place to stay if you are in town for a special event.

Oct 14 – 21

€ 137 per night