Lovingston, Virginia
Historic Virginia Bed and Breakfast on 14-acre estate with vineyard, salt-water pool and charming rooms—ideal for a wine-country getaway near Charlottesville.
Winter is an ideal time to experience Monticello Tours, especially for those seeking a more thoughtful and uncrowded way to explore one of Virginia’s most significant historic sites. Located just outside Charlottesville, the Monticello plantation offers an in-depth look at the Thomas Jefferson House, his architectural vision, and the layered and complicated history.
Monticello is open year-round, and winter visits often allow for a slower pace and more time to engage with the stories presented throughout the home and grounds. Guided Monticello Tours focus on the main floor of the Thomas Jefferson House, where Jefferson lived, hosted guests, and pursued his interests in science, agriculture, and design. Visitors gain insight into both his accomplishments and the contradictions that shaped his legacy, making this one of the most impactful historic tours in Virginia.
Beyond the house itself, exhibits and outdoor spaces explore the lives of the enslaved men, women, and children who labored at Monticello. These interpretations are presented with care and honesty, offering a fuller understanding of the plantation’s history and its lasting significance.
Winter is also a wonderful season to explore what to do in Charlottesville, VA. After your tour, head into town to visit the Historic Downtown Mall for lunch, coffee, or local shopping. The University of Virginia campus offers another meaningful historic experience, and nearby wineries remain open for tastings throughout the season.
Choosing the right lodging completes your winter getaway. Staying at a bed and breakfast near Charlottesville puts you within easy driving distance of Monticello while offering a comfortable place to unwind after a day of exploring. Guests enjoy welcoming common spaces, cozy evenings by the fire, and thoughtful amenities that make winter travel feel extra special.
The Orchard House Bed and Breakfast is set in Virginia’s wine country, and it’s an excellent location to relax and make your home base. This B&B is designed with elegantly muted tones, unique florals, patterned wallpaper, and both modern and antique furnishings.
From historic tours to wine tastings and seasonal events, there are so many things to do in Charlottesville for a truly unique winter getaway in Virginia.