House holiday rentals in Charlottesville

Cabin in Woods | Family & Dog Friendly | Fire Pit

Welcome to the Wooder House, a cozy haven nestled in the woods of Virginia's beautiful Nelson County! Enjoy relaxing and connecting in a private home centered on 38 wooded acres, but close to NelCo fun! - Peaceful nature retreat - Outdoor patio & fire pit - Great for families & dogs - Fully stocked kitchen - Private trail + hiking options nearby - 8+ min. to wineries, breweries, cideries, restaurants - 25 min. to Wintergreen Resort For more photos and fun, check us out on IG: @thewooderhouse

One Level Living at Shadwell Terrace

Set in the heart of Wine Enthusiast’s Wine Region of the Year, this newly renovated 2-bedroom, 800 sq/ft terrace level flat with separate entrance, is located in a private setting in the Keswick area. Close to Downtown Charlottesville, we are adjacent to Clifton Inn and Glenmore and minutes to Keswick Hall. After exploring many of Virginia’s wineries, breweries, and historical sites, kick your feet up between the trees in the hammock or share your adventures online with our high speed Wi-Fi.

Gorgeous Modern Mountain Home + Blue Ridge Views

GREENWOOD VISTA - Escape to our modern mountain retreat nestled along the Blue Ridge mountains. Whether you want to explore Shenandoah National Park, visit wineries, or relax in our hot tub with stunning mountain views, this gorgeous A-Frame home is the perfect place for you. We have thoughtfully appointed our home with everything you need to be comfortable. From a luxurious master suite, fully equipped kitchen, to coffee and wet bar, sauna, outdoor grill, billiard table, and plenty of games.

Belmont Private Suite, 1/2 mile to Downtown Mall

Cozy, quiet high-ceiling basement suite located in historic Belmont neighborhood. Private entrance with keypad lock for easy check-in/out. Space includes living area, 1 large bedroom with queen bed (air mattress provided if needed), full bathroom with towels/essentials, coffee maker, electric tea kettle, microwave and mini fridge. Walking distance to Downtown mall and numerous restaurants, coffee shops, and parks nearby. 1-2 mile walk from UVA and 3 miles to Monticello. Free street parking.

Wine weekends!

This listing is properly registered with the City & abides by local ordinances. Large beautifully renovated and thoughtfully appointed home is walkable to Scott Stadium (1.3m), under 3 miles to Downtown Mall, close to UVA/hospital, shopping, dining & all Cville has to offer! Perfect for getaways, weddings, bachelorettes. Game room w/ pool table and foos ball! Easy access to vineyards/breweries/trails. Great amenities (snacks, toiletries, coffee, Wi-Fi, washer/dryer, sheets, towels).

Woodwind Cottage

Woodwind Cottage is a brand new, beautifully built cottage with living room, bedroom, bath, kitchen and loft. It has charming architectural details and a covered porch for enjoying the view of the woods. The loft has a fold out sofa for an extra guest or private work space. The home has wifi, smart tv for streaming, and a gas fireplace. Enjoy reading in the oversized window seat, rise early to see deer in the yard or, perhaps, a hot air balloon overhead in the spring and fall.

Cavalier Cottage-3 BR/Bath, Calm Amid UVA Grounds

Fully-updated, custom home in premier location. Warm hardwoods, lots of light, comfortable sofas & beds, easy check-in -- we strive to make your stay restful and refreshing. Nestled between Scott Stadium & JPJ, O'Hill & the Rotunda, wine country & the downtown mall, you could not be closer to the action yet in a quiet, residential neighborhood. The perfect place for any & all Cville/UVA events, work trips, reunions, weddings, family vacations, college visits, etc.

Greenleaf Grove

Charming 1947 Cape Cod Style home with three bedrooms and two updated bathrooms. The upstairs is big attic space with double bed and private bathroom. Modern kitchen with all new amenities. The home is 1.7 miles from UVA Rotunda and walking distance to parks, restaurants and downtown mall. Open to inquiries about any dates that do not appear open on calendar and price reduction for visits greater than 7 days

The Carriage House at Wine Cellar Circle

Just steps from all the best Charlottesville has to offer, make yourself at home in this impeccably designed carriage house! You'll enjoy soaring ceilings, huge picture windows, a luxury galley kitchen, a modern, tiled bathroom and a comfortable bed. Perfect for a romantic getaway or a weekend with friends and family, explore Charlottesville in style from the Carriage House at Wine Cellar Circle!