Holiday rentals with a pool in Charlottesville

18th Century Charming Bungalow #127 Pool & Spa

Escape & unwind from city life on a beautiful historic, 250 acre estate 20 minutes from Charlottesville! Our historic bungalow is perfect for those who want to take a step back in history and enjoy the wonder nature has to offer! Steep stairs access the upstairs bedroom, 2 can sleep downstairs. We are only 20 min away from Jefferson's "Monticello" & from James Madison's " Montpelier". Treat yourself to an onsite certified massage with a wellness therapist.Please book online at Spagreensprings.

Mountain Cottage, beautiful Views, Nelson 151

Wake to gorgeous Mountain views & rolling green meadows bordering the Rockfish River on our family estate. Private attached unit with built in pool (mid April-mid Sept)in the Blue Ridge mountains of Nelson County Virginia on the center of the 151 Brew Ridge Trail. Much preparation has gone into making your stay beautiful, convenient and comfy. No need to physically interact if that’s your desire. Enjoy swimming, hiking, kayaking, horse back riding, skiing, snowboarding, and more! 3 nite minimum

Private Apt in Historic C'ville Home (Garden Side)

This cozy, newly refurbished, 1 BR/1 Bath, apartment is attached to a historic Charlottesville home. With just a 10 min walk to the Downtown Mall and a short drive to the university hospital/campus, the location is nestled in the heart of C'ville. Special amenities include a Sleep Number bed, fast Wifi, a 50" Smart TV with access to Amazon Prime and Netflix, access to pool use during the summer, and Park Lane street parking. Hand crafted soapstone counters and farm sink, beautiful new tile work.

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.

Rivanna Farm Estate North I Pickleball I Pool

This historic 42-acre country estate features four distinct residences, three of which are Airbnb rentals. The "North” offers beautiful views of the Blue Ridge Mountains and includes 4 bedrooms: 2 bedrooms with queen beds, and another with 2 twin beds on the main floor, and an additional queen bedroom upstairs. The second floor has a full kitchen, living room, & dining area. On the lower level is a yoga studio, game room, outdoor patio area w/seating, and charcoal bbq. (Charcoal not provided)

Unique OASIS - Silo Barn - Swim Pond- 5 Miles Trai

4 unique rentals available (click our profile)! Unwind at this Central VA Country Paradise! Stay in a converted Barn & Silo w/ private natural swim pond and waterfall tucked into the woods on 140 Acres! Your own Oasis awaits, step out on your porch for coffee/drinks with the farm animals. Take a hike around the Lake on the 5+ miles of trails before cooling off in the pond while you gaze up at the stars. Sheep, Dwarf Fainting goats(next to silo 10' away), Chickens, Ducks, Bunnies, & Turkeys.

Yurt*POOLpeace*FARM*horses*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 Nov 20- March 1.) Check out Cair Paravel Farmstead on FB/the web to see all we have to offer.

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.

Blue Ridge Bliss - For family & friends to enjoy!

Welcome to Blue Ridge Bliss! Come enjoy the mesmerizing mountain top views of this well-appointed condo in The Ledges of Wintergreen Resort. It’s the perfect place to unwind, unplug and recharge. Whether here to ski, hike, or visit Virginia wineries, cideries, or craft breweries you’re sure to enjoy the beautiful views from the living room and deck. A short walk to The Highlands lift and across the street from Fire & Frost eatery and the Wintergreen Spa, this is an ideal location.

1 bedroom condo, hiking, breweries, wineries

Enjoy the mountains in the spring & summer enjoy hiking or a swim in the heapool! 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, all you need for a quiet getaway

Mountain View Nest

From the moment you walk in, this condo offers endless opportunities to relax and retreat. The sweeping mountain views over the back deck provide the ideal setting for a romantic getaway, a girls weekend, or much needed time to recharge. This one bedroom/bathroom unit with a king sized bed, fully stocked kitchen, and artistic decor is located on the third floor of the Ledges. It is the perfect location for those who ski, hike, golf, or taste the flavors from local wineries.

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. 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 a Great Pyrenees for cocktails. Feel like staying in - SmartTVs with YouTubeTV (which includes local channels) and Gig-speed Internet await. Easy checkout. No cleaning fee.