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9 Romantic Getaways In Charlottesville, Virginia

Published:

Modified: 5 October 2026

by Katee Savoy

9 Romantic Getaways In Charlottesville, Virginia

Charlottesville, Virginia, offers nine romantic getaways: The Clifton, Boar's Head Resort, Keswick Hall, The Inn at Willow Grove, Trump Winery, Pippin Hill Farm & Vineyards, Monticello, Carter Mountain Orchard, and Ash Lawn-Highland. These range from historic estates and luxury resorts to working vineyards and orchards.

The Clifton

The Clifton is an 18th-century estate surrounded by gardens. It provides a retreat for couples seeking an escape.

Boar's Head Resort

At the foot of the Blue Ridge Mountains, the Boar's Head Resort has a championship golf course, spa, and dining options. Couples can stroll through the gardens or eat at the restaurant. The resort offers a romantic getaway in Charlottesville, Virginia.

Keswick Hall

Keswick Hall is a mansion set amidst rolling hills. It provides a sanctuary for couples seeking a retreat, with accommodations and dining experiences. Keswick Hall creates a backdrop for romantic getaways in Charlottesville, Virginia.

The Inn at Willow Grove

The Inn at Willow Grove is a restored plantation house in the countryside. It offers suites, gourmet dining, and surroundings. Guests can walk through the gardens or unwind in the accommodations. The Inn at Willow Grove provides an atmosphere of romance and hospitality.

Trump Winery

Situated amidst vineyards, Trump Winery is a destination for couples seeking an escape. The estate offers vineyard tours, wine tastings, and accommodations. The ambiance and vistas make Trump Winery a setting for getaways, where couples can savor wines in Charlottesville, Virginia.

Pippin Hill Farm & Vineyards

Perched atop the Monticello Wine Trail, Pippin Hill Farm & Vineyards has views of the Blue Ridge Mountains and vineyards. This estate offers a backdrop for celebrations and escapes. From wine tastings to picnics on the grounds, Pippin Hill Farm & Vineyards sets the stage for romantic getaways in Charlottesville, Virginia.

Monticello

Monticello invites couples to immerse themselves in the legacy of Thomas Jefferson. This estate, nestled amidst rolling hills and gardens, offers a blend of romance and heritage. Couples can explore the historic house, stroll through the grounds, and revel in the vistas. The estate also serves as a key stop for those interested in historic homes and landmarks in Virginia.

Carter Mountain Orchard

Perched atop the Blue Ridge Mountains, Carter Mountain Orchard is a retreat with rustic charm. The orchard offers an escape where couples can partake in apple picking, savor baked goods, and relish views of the countryside. Whether enjoying a picnic or sipping artisanal ciders, Carter Mountain Orchard provides a setting for couples to bask in the natural wonders of Charlottesville, Virginia.

Ash Lawn-Highland

Ash Lawn-Highland is an estate that offers couples a glimpse into the life of James Monroe. Set against rolling hills and landscapes, this historic retreat invites couples to wander through the gardens, explore the preserved mansion, and immerse themselves in the estate. With its heritage and ambiance, Ash Lawn-Highland provides a setting for romantic getaways in Charlottesville, Virginia. Like Monticello, it is another of the region's historic homes and landmarks in Virginia.

FAQs

Q: What are some popular outdoor activities for couples in Charlottesville?
A: Couples visiting Charlottesville can enjoy outdoor activities, including hiking along the trails of Shenandoah National Park, exploring the gardens at Monticello, or embarking on a hot air balloon ride over the landscapes. These opportunities connect directly to hiking and the outdoors in Virginia and hidden trails and gems in Virginia.

Q: Are there any romantic dining options in Charlottesville?
A: Charlottesville boasts romantic dining options, from intimate farm-to-table restaurants to cafes and wineries. Couples can indulge in cuisine while savoring the ambiance of the city's culinary scene.