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

Yurt in Stanardsville

4.95 out of 5 average rating, 1,160 reviews

Yurt*POOLpeace*horses*farm*goats*woods*STARS*Hotub

Come experience living in a round structure filled with amenities-fully equipped kitchen, deep tub, heating and AC, hot tub and in ground pool. Great for couples, friends, and families. A 10 minute hike gets you into Shenandoah National Park, explore our 58 acres on numerous walking trails, visit Charlottesville, historical sites, caves, or play in rivers. Child friendly- no pets. Private hot tub Labor Day-Memorial Day. Check out Cair Paravel Farmstead on FB/the web to see all we have to offer.

Superhost

Farm stay in Charlottesville

4.9 out of 5 average rating, 141 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.

Guest favorite

Rental unit in Madison

4.9 out of 5 average rating, 247 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*

Guest favorite

Condo in Wintergreen Resort

5 out of 5 average rating, 103 reviews

1 bedroom condo close to hiking breweries & resort

Enjoy the mountains in the spring & summer enjoy hiking or a swim in the pool! 1BR 1BA centrally located in Wintergreen 5 minute walk to Wintergreen resort Close to many hiking trails Enjoy the many breweries & wineries in the area Mountaintop Market is across the street 1 Bedroom 1 Bath & New queen sleeper sofa Stocked kitchen, cookware, spices & cooking oils Premium coffee & assorted tea Private furnished patio Wood burning fireplace (wood provided) flat screen TV w/ streaming channels

Guest favorite

Guesthouse in Charlottesville

5 out of 5 average rating, 119 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.

Guest favorite

Home in Robertson

4.92 out of 5 average rating, 204 reviews

One Of A Kind Home in VA Wine Country on 50 acres

Welcome to Lumusa Lodge. Leave your cares behind as you turn onto the windy road that leads you to this beautiful 50-acre retreat. We are proud to share our home and hope your time here is rejuvenating. Designed/built by a Hollywood actor and situated in wine country, this home is an hour from Dulles, 45 minutes from Charlottesville & 15 minutes from Culpeper. We have an adjacent farmhouse if you need additional space. Great venue for weddings, bachelorettes, and other special events.

Guest favorite

Cabin in Culpeper

4.97 out of 5 average rating, 176 reviews

Comfortable and unique 1790's log cabin

Recently restored 1790's log cabin with modern amenities on a 30 acre horse farm. Secluded wooded setting with pond view, less than 1,000 feet from main house and only 5 miles from downtown Culpeper with it's fine dining and quaint shops. Take a short drive to scenic Shenandoah hiking & biking trails, local vineyards and distilleries, Civil War sites, Commonwealth Equestrian Park, stroll around the farm or just unwind on the front porch or in front of the wood stove with a good book.

Guest favorite

Cabin in Gordonsville

4.82 out of 5 average rating, 247 reviews

1700's Summer Kitchen Cottage #147 Pool & Spa

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. This is 20 minutes away from Jefferson's Monticello & James Madison's "Montpelier" . Treat yourself to an onsite certified massage with a wellness therapist. Please book online at Spagreensprings.

Guest favorite

Guesthouse in Troy

4.99 out of 5 average rating, 155 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.

Guest favorite

Home in Lovingston

4.95 out of 5 average rating, 199 reviews

Private, Covered, Heated Year-Round Pool & Hot Tub

Experience the Blue Ridge Mountains and country life of central Virginia and enjoy everything Nelson County has to offer. The Cottage on the Knoll is a comfortable 3br/2bth that’s centrally located in Nelson County, offering the perfect mix of modern comfort and country charm. The Nelson 29 and Nelson 151 craft beverage trails await you, while plenty of hiking, fishing, and mountain views will appease any outdoor recreation lover or nature enthusiast, making it the perfect getaway.

Guest favorite

Bungalow in Stanardsville

4.93 out of 5 average rating, 258 reviews

Romantic, Carriage House Studio at Fairhill Farm

Delight in the bold views of the Blue Ridge Mountains while lounging on your private deck at the Carriage House on Fairhill Farm. Stroll on 150 acres. Hike our private trails. Fish in private pond or river. Enjoy pool. Delight in farm animals including our miniature horses. Located 2 hours southwest of Washington, DC, 1 1/2 hours east of Richmond and 25 minutes north of Charlottesville, VA. Near Shenandoah National Park, Monticello, Montpelier, Ash Lawn, and UVA

Guest favorite

Farm stay in Barboursville

4.98 out of 5 average rating, 202 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!