One of the most rewarding journeys you can take in Virginia is to Monticello, the iconic mountaintop estate that was the lifelong project of Thomas Jefferson, third president of the United States and author of the Declaration of Independence. Many of our guests enjoy taking Monticello tours, as it sits just outside Charlottesville and is recognized not only as a historic house museum and presidential library, but also as a UNESCO World Heritage Site.
As one of the best things to do in Charlottesville, VA, exploring this plantation home on Monticello tours holds the number one spot on TripAdvisor for area attractions. You can always include a trip to the quaint downtown after touring this impressive home, garden, and mountaintop trails. Monticello is open year-round with rotating events and exhibitions, so even in the winter, it’s a great addition to your itinerary exploring Virginia’s wine country in Nelson County.
Including historic tours in Virginia adds a well-rounded feel to getaways and group trips. You can spend some time reflecting on the historic figures who called this area home, the architecture, and all the stories of the past. Before you start planning your tours of Monticello and Charlottesville, you’ll want to secure your lodging, and our Bed and Breakfast near Charlottesville, VA, offers a luxurious place to settle in and unwind. Plan your winter trip to Virginia and book your room today!

Explore Rich History & Stories on Monticello Tours this Winter
Located just a short drive from Lovingston, Monticello offers a powerful and engaging look into American history, architecture, and the complex legacy of Thomas Jefferson. If you’re looking for what to do in Charlottesville, VA, before you visit, this iconic destination deserves a top spot on your itinerary. From its mountaintop views to its thoughtfully curated tours, this historic site offers insights that stay with you long after you return home.
Here is everything you need to know before you book a Monticello Tour this winter:
- Monticello is best known as the Thomas Jefferson House, designed and continually refined by Jefferson himself. His passion for architecture, innovation, and learning is evident in every detail, from the neoclassical design to the clever built-in furnishings and the natural light throughout the home.
- Monticello Tours typically include guided access to the main floor of the house, where guests learn how Jefferson lived, worked, and entertained. The experience goes well beyond furniture and décor. Visitors gain a deeper understanding of Jefferson’s ideas, his global influences, and the contradictions that shaped his life and legacy.
- A visit to Monticello also includes poignant interpretations of the Monticello plantation and the lives of the enslaved men, women, and children who lived and labored there. These stories are thoughtfully presented through exhibits, guided tours, and outdoor spaces that encourage reflection and learning. Monticello is widely recognized for offering some of the most comprehensive and honest historic tours in Virginia.
- Book tours in advance online; there are multiple options for shorter visits, including just a guided tour of the Thomas Jefferson house, or more extended visits that take you through the grounds and gardens.
More Things to Do in Charlottesville nearby:
- One of our favorite ways to extend your day in town is heading out on Monticello wine tours. The surrounding countryside is home to acclaimed Virginia wineries, many inspired by Jefferson’s early interest in European winemaking. Head to the historic Jefferson Vineyards or the modern Virginia Wine Collective in downtown Charlottesville.
- Another fantastic historic tour in Charlottesville is the beautiful University of Virginia campus. The sweeping grounds are peppered with ancient trees and prominent architecture.
- The Historic Downtown Mall in Charlottesville is a fantastic place to find farm-fresh lunch options, a coffee shop, or local boutiques for souvenirs. The tree-lined brick street is closed to pedestrians only. The Paramount Theater anchors the open-air mall, and if you plan ahead and book tickets for a show, it’s an excellent addition to any getaway to Virginia.
- Carter Mountain Orchard is open year-round, and while you might not be able to pick your own fruit in the winter, the apple cider donuts are fresh and fried all winter long. Pop by here to grab a sweet treat and a glass of wine.

Reserve a Stay at our Bed and Breakfast near Charlottesville, VA
Each morning of your stay at our Bed and Breakfast near Charlottesville will begin in our airy and light-filled dining room. Guests rave about our freshly baked treats and brewed coffee, helping them start the day off on the right foot. After a leisurely breakfast, head out on the scenic and easy drive to Monticello, about 45 minutes north. Along the way back, be sure to stop off at one of the best wineries in Virginia, Loving Cup Vineyard is always a lovely stop.
On a cozy winter evening, our guests often relax by the fire or retreat to their private room for a quiet night in. Our beautifully restored main house features six elegantly appointed guest rooms, each with a private en suite bath and a cozy seating area. Our stand-alone farmhouse, with the same Southern comfort style and design, has three rooms and can sleep up to eight for group or family vacations.
During your stay, if you’d like to add a special touch or two, we have some thoughtful extras, including a couples massage, multi-course meals, in-room wine, or breakfast delivery. These perks make anniversaries or milestones even more recognized for the special celebration that they are, and we can’t wait to be a part of them. Start planning your next getaway in Virginia, filled with Monticello tours, the best things to do in Charlottesville, and local wine tastings. Book your lodging today!