Experience award-winning wineries, breathtaking views, and unique attractions with an overnight stay in Charlottesville and Albemarle County, Virginia
As the air begins to chill and the foliage turns toward the vibrant colors of fall, the Charlottesville, Virginia area, located just two hours outside of Washington, DC, transforms into a magical destination. Wine amateurs and aficionados alike flock to taste the region’s history through wine and to celebrate Virginia Wine Month throughout October. With more than 40 wineries of all shapes and sizes along the Monticello Wine Trail—many of which take home major accolades each year at the Virginia Governor’s Cup, the state’s annual and esteemed wine competition—it’s no surprise that Charlottesville and Albemarle County stand out as the premiere destination for a fall getaway.
When you’ve gotten your fill of award-winning wine, there’s much more to explore. The Charlottesville area has been named a top dining destination for a city of its size, with farm-to-table restaurants at every turn. Stroll the historic pedestrian Downtown Mall for dozens of restaurants with patio dining, cafes, boutique shops, and entertainment venues like the Paramount Theater or the Ting Pavilion. The downtown area also features a robust art scene with many galleries, exhibits, and live music and is only minutes from breathtaking scenic parks and abundant outdoor activities.
With so much to discover, an overnight stay in the Charlottesville area is a must. During the fall, visitors can enjoy dazzling foliage while hiking along the Blue Ridge Mountains, family-friendly apple picking at local farms, shopping at weekend farmers markets, and so much more. For midweek stays, visitors can experience all that Charlottesville has to offer while enjoying fewer crowds and affordable lodging. For a truly unique experience, embark on a sip-and-stay vacation at one of the Charlottesville area’s premium wineries that offer on-site lodging and immersive experiences.
Winery Lodging in Charlottesville & Albemarle County
Find your perfect pairing along the Monticello Wine Trail, beginning with some of these wineries and vineyards offering on-site lodging
This impressive wine country estate is one of the most prestigious and architecturally significant residences in history. Located at the foot of Virginia’s largest vineyard, Trump Winery, the 45-room estate epitomizes luxurious country living, complete with tasting rooms, expansive gardens, and a private dining room exclusive to hotel guests.
This 14-acre sanctuary offers gorgeous views of the vineyard and the surrounding landscape. Guests who stay at the bed-and-breakfast will be treated to a glass of local wine on check-in day, a wine fridge stocked with a bottle of sparkling wine, farm-fresh country breakfasts, and a back deck perfect for lounging and watching wildlife.
While located conveniently near Charlottesville-Albemarle Airport, the farm setting of Chisholm Vineyards is insulated from the hustle and bustle of city life. The Lake House is situated on a 500-acre farm that boasts beautiful views of the pond and the Blue Ridge Mountains. Enjoy peace and quiet as you sip on wine made exclusively at the estate.
This winery offers tastings in a custom-designed tropical greenhouse and is home to a gorgeous bed-and-breakfast that overlooks the vineyard and Blue Ridge Mountains. Bring the whole family or a group of friends to rent out the entire house for a private weekend full of wine and fun.
Along the Monticello Wine Trail, guests can choose between quaint cottages, brick Georgians, and historic manor home accommodations during their stay at this 5,000-acre reserve. Each stay comes with access to Mount Ida’s private lake and the on-site tasting room and taphouse, where guests can enjoy seasonal menus and frequent wine and craft beer pairings.
The Crossroads Inn at Pippin Hill has been accommodating travelers since it was built in 1820. Located in the Mid-Way Tasting Triangle, it’s where guests can enjoy close proximity to cideries, vineyards, and wineries, with the closest being Pippin Hill Farm & Vineyards just a three-minute walk from the inn. For an unforgettable stay, there’s private dining at the vintner’s table with a custom four- or five-course dinner paired with Pippin Hill wines.
A modern-country bed-and-breakfast with panoramic mountain views hides amongst the vines at Stinson Vineyards. Guests can enjoy laid-back luxury on the property, which offers daily three-course breakfasts, wine dinners in the cellar, and the chance to admire the majestic views from the comfort of the heated pool and outdoor patio.
Located just 5 miles from downtown Charlottesville, Virginia, the Winery Cottage at Eastwood is a food-and-wine destination. Guests can stay in the charming three-bedroom home and enjoy award-winning wines made with grapes, apples, and pears grown on the property, and artfully prepared farm-to-table menus that complement their robust lineup of wines, beers, and ciders.
Whether you’re looking for a quaint stay or a posh retreat, there are plenty of options to have a delightful sip-and-stay vineyard vacation in Charlottesville and Albemarle County.
Plan your stay today at visitcharlottesville.org
20+ Award-Winning Wineries On the Monticello Wine Trail in Charlottesville & Albemarle County, Virginia
Escape to the Monticello Wine Trail of Virginia Wine Country in Albemarle County and plot your visit to 21 award-winning wineries.
What began as a single vineyard in the 1970s, the Monticello Wine Trail has grown into more than forty internationally acclaimed wineries in Virginia.
- by Amber Chase
- by TLP Editors
- by Hannah Lee Leidy