Vacation Rentals

Charlottesville Insider's featured listings are perfect for travelers looking for a more secluded and luxurious vacation experience. Browse our selection of private vacation rentals in Charlottesville located near popular attractions like the University of Virginia, Monticello, Shenandoah National Park, and vineyards along the Monticello Wine Trail.

Rockfish Ranch

Family Reunions, Weddings, Corporate Retreats - Featuring 120 Acre Estate w/ 2500ft of Pristine River, Lodge, Cabin, Cottage, Sauna, and Hot Tub

Corner House

Stylish Belmont Home, Walk to Downtown Mall and enjoy all that Belmont has to offer.

Afton Mountain Vineyards

Afton Mountain Vineyards provides the perfect backdrop for a romantic getaway or family vacation. All of the vacation rentals are beautifully furnished with modern amenities to make your stay comfortable and enjoyable.

High Street Inn

As you arrive, you'll be greeted by the charm of a beautifully preserved Mediterranean villa, dating back to the 1900s. The stucco façade, adorned with classic Spanish tiles, opens up to lush gardens, private terraces, and a meticulously landscaped outdoor patio—a true oasis in the middle of the city. High Street Inn is entirely self-service, providing you with the utmost privacy and convenience.

Water Street Condo

Modern Downtown Retreat w/ Rooftop Terrace, Across from The Ting Pavilion, 1 Block Off Downtown Mall. Overlooks the C&O Railway.

Waterperry Farm

Twenty minutes from historic Charlottesville, in the lush countryside of Albemarle County, there’s a magical place called Waterperry Farm.

The Cottage at Eastwood Farm and Winery

The Winery Cottage at Eastwood Farm and Winery is located on the historic Woodland estate, built and owned by Jefferson builder, John Dunkum in 1810. Our 78 Cville acres include our family’s winery with indoor (year round) and outdoor (Apr-Nov.) tasting rooms, extensive wooded trails, incredible mountain views and apple orchard. Nestled on the same ridge as Monticello, Carter's Mtn, Jefferson Vineyards, Blenheim and Trump Vineyards. Five minutes to Belmont and Downtown Mall.

Colle

Historic Estate w/ land granted by Jefferson & where the first wine grapes were planted in 1773. Today, wine culture flows strong as the home of Jefferson Vineyards.

The Townsman Hotel

The Townsman is unlike your typical hotel. That’s why we call it the unhotel. Poised just above Charlottesville’s bustling Downtown Mall with no staff and no front desk, it feels like a well-kept secret right in the center of all the action.

The Gatsby

Direct access to the Charlottesville Downtown Mall, you'll find yourself just steps away from a plethora of exciting activities and attractions.

Old Met #202

One bedroom Downtown Mall Fronting w/ Corner Windows Overlooking the Bricks of the Downtown Mall. Parking Included.

Magnolia Hill

To arrive at Magnolia Hill is to exhale and surrender to airy elegance in a one-and-a-half-acre park-like setting just five minutes from downtown Charlottesville and the University

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