Holiday houses in Charlottesville

Cozy Mountain Cottage on Brew/Wine Trail-King Bed

Welcome to the Sugah Shack, a cozy, beautifully appointed new construction cottage nestled in the foothills of the Blue Ridge Mountains! Located midway on the Brew Ridge Trail, but 500 yards off the byway, so guests have a quiet retreat. Perfect for romantic getaways, destination telework space, or families exploring this outdoor paradise community. Stunning property boasts beautiful vistas with sweeping 300-degree mountain and a year-round calendar of outdoor activities. GAS FIREPLACE/FIREPIT

Idyllic Cottage Retreat

⭐️ Condé Nast Traveler Approved ⭐️ Cozy cottage nestled on a historic 400-acre Blue Ridge Mountain farm abutting Shenandoah National Park. Every space inside this cozy cottage is creatively styled, with tons of perfectly imperfect charm. Outside, a hammock beneath the elm trees, fire pit and grill, all allow for enjoying the splendor of this peaceful enclave. Excellent day-tripping to many of central Virginia's celebrated wineries and breweries, as well as scenic drives and hiking trails.

Green Willow Farm apartment near Monticello

*Winter update: Jan/mid-March. Our fairly long flat gravel driveway is hard to navigate in snow. AWD, or heavier cars, are helpful. We will shovel some, allow sun to melt the remaining. FYI when booking. Spacious farm apartment(walkout apt below our living space) in the rolling hills of Virginia. Galley kitchen. Large fireplace. Private entrance. Stone patio. Close to downtown Charlottesville and UVA(+/- 8 miles). A few miles from Monticello, Many vineyards, and Carter's Mountain Orchard.

Lux Country Retreat minutes from Charlottesville!

Located just off route 29 this private luxury retreat with surrounding 2 acre fenced yard is one mile from Pippin Hill Farm & Vineyard and only 15 minutes from UVA/Charlottesville. You will find this home spacious, bright and airy, perfect for entertaining groups or families. The house is completely equipped with everything you may need to host the perfect getaway! Nearby attractions: Pippin Hill, Albemarle Ciderworks, Ragged Branch Distillery, Potter's Craft Cider and Charlottesville!

The Laurel Hill Treehouse

Fully immerse yourself in nature in this serene Scandinavian-inspired woodland retreat, perfect for a couple's getaway. The treehouse is perfectly nestled amongst the trees, offering a chance to unwind while enjoying the beautiful views of nature. Just imagine yourself relaxing on the wrap around porch, soaking in the hot tub, cooling off in the creek, & cozying up to a crackling fire. We invite you to unwind, reconnect with nature & create cherished memories in this tranquil hideaway.

Honey B - Beautiful loft near UVA, Monticello

Best of both worlds! In beautiful nature but close to UVA, Monticello and downtown. Honey B (Honey House 2) has a lofty feel with the footprint of a small house. High ceilings and several skylights allow for light and privacy in the quiet neighborhood, Located on the southwest side of Charlottesville, just 7 minutes to Scott Stadium, UVA campus, and restaurants, 10 minutes to historic downtown mall, Thomas Jefferson’s Monticello and central to many major wineries and breweries.

Tranquil Cottage sleeps 5

An adorable home with breathtaking sunsets over the Blue Ridge mountains. We are 4 miles to downtown and minutes to many vineyards, shows and restaurants. Enjoy comfortable beds, the fire pit with Adirondack chairs, big skies filled with stars and animals. Walk our country roads, feed the horses, enjoy the views of the mountains and meadows. Base price is for 2 people, no pets or children under 8 for safety. Stays more than 3 nights will have an added cleaning fee of 20.00

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.

The Loft at Minor Mill - Private loft apartment.

Our place is a newly constructed barn loft in our 1960's barn. Enjoy beautiful views of the surrounding countryside from large windows and a private balcony. The barn is surrounded by our horse pastures and neighboring fields. Self check in with the key lockbox. This loft is separate from the main house where we live. Private parking and entrance for our guests directly outside of barn loft (this is separate from the main house driveway).

Luxury tiny house 3 min from UVA

La Casita is a new tiny home combining modern luxury with central location adjacent to UVA, central to wineries, and 10 minutes from Monticello. La Casita is design built to offer custom furnishings and luxurious touches. We are in the residential pedestrian-friendly neighborhood of Fry's Spring, near I 64. Walk to restaurants and Scott Stadium. Enjoy all amenities including a high-speed internet.

Beautiful, Cozy, Downtown Apt!

Enjoy a stylish experience at this centrally-located place. Beautifully curated apartment with luxury kitchen, tiled bathroom and wonderful deck. It has two split units to keep the place as cool or as warm as you desire. Semi-firm Queen mattress for a perfect nights sleep. A short walk to the Historic Downtown Malls shops and restaurants and The Rivanna River for tubing, swimming, biking, picnics.

2 King/1 Twin Close to Downtown & UVA

⭐️Two bedroom lower-level apartment (2 king beds, 1 twin XL, 1 toddler bed, 1 pack-n-play) in a quiet neighborhood near downtown! ⭐️Our guests rave about the excellent value, amenities, & cleanliness! 📍1 mile from UVA Hospital and Downtown Mall 📍1.6 miles from UVA ⭐️No smoking! ⭐️Please read note about the slope to the entrance 🟢The person booking must be present during the stay.