WHERE TO STAY
First, pick a home base
If wine tastings are a key part of your Charlottesville vacation itinerary, The Clifton is where you want to stay. This historic estate is located on 100 acres of countryside in view of the Blue Ridge Mountains and smack dab in the middle of Virginia wine country. Its secluded spot means that besides wine tasting, there is hiking and other outdoor activities nearby, too. Plus, there’s a fancy restaurant and wine cellar on site, so this is far from “roughing it.”
The Townsman really isn’t a hotel, it’s more like a short-term rental or bed and breakfast -- but minus all the staff, to keep costs down. They call it an “unhotel” because there are only four rooms (which start around $189 a night for weekends in June), and all operations are handled solely online (there’s not even a hotel phone number). Unlike some other short-term rentals in town, though, this one boasts one of the most prime addresses in Charlottesville, as it’s right on the Downtown Mall, aka the city’s walkable main drag with restaurants, shops, and nightlife.
If you want to get a feel for Charlottesville’s history, the Oakhurst Inn is the spot to call home base. This boutique hotel has a B&B vibe and is located right in the city’s National Historic District, just across the street from UVA -- so be sure to explore the grounds, including the famed Lawn and Rotunda. Getting to the center of town won’t take long, as there’s a free trolley from the UVA campus to the Downtown Mall. If you’re feeling extra studious, you can curl up with a book at one of the hotel’s four libraries, too. You won’t have to leave the hotel for one of the top breakfasts in the city, either: The Oakhurst Inn Cafe (worth a stop even if you’re not staying here) serves up locally-sourced takes on classic Southern dishes alongside an espresso bar stocked with beans from a nearby coffee roaster.
Omni Charlottesville Hotel
Located in a central spot next to the Downtown Mall and with plenty of luxury vibes, the Omni has everything needed to keep you well rested throughout your stay. Besides cushy beds and an indoor and outdoor pool, the spot is known for its seven-story atrium and garden, a perfect spot to sip your morning coffee. Also, because of its central location, you can park your car here when you check in and visit everything on foot throughout your trip.