Sip and Stay: Winery Lodging

Sip & Stay at These Charlottesville Area Wineries

There are 40+ wineries in the Charlottesville & Albemarle County area, including several that offer on-site lodging. Our region's wineries have received accolades in recent years and the region, the Monticello AVA, was named one of the top wine destinations in the world by Wine Enthusiast!

(Header photo courtesy of Bekah Imagery)

Here’s a look into some great options for the perfect sip & stay vineyard vacation!

Albemarle Estate

Albemarle Estate is a luxurious wine country estate surrounded by vineyards and beautiful countryside. Located at the foot of Virginia’s largest vineyard (Trump Winery), this 26,000 square-foot mansion is the ultimate in luxury. Reminiscent of a classic Georgian-style home, the 45-room estate epitomizes high-style country living in the tradition of an English manor, complete with mountain views and expertly-tended gardens.

The Clementine Cottage at Merrie Mill Farm & Vineyard

Stay next door to the Tasting Room at Merrie Mill Farm. This delightful cottage is perfect for a romantic getaway, fun couples’ weekend, or family holiday. Eclectically designed, the Clementine Cottage offers 2 bedrooms, 1.5 bathrooms, kitchen, sitting room, and laundry.

The Cottage at Eastwood Farm and Winery

The Cottage at Eastwood Farm and Winery is a quaint home featuring three bedrooms, a bathroom, full kitchen, and living rooms and dining rooms. Guests can stay for just a weekend, or longer if they desire, and dogs are also welcome. The Eastwood Farm and Winery is in the heart of Virginia’s Wine Country, and visitors will be able to enjoy award-winning wines and ciders surrounded by the beautiful Carter’s Mountain range. Besides their grape vineyards, Eastwood also grows apples and pears, which they use to create their White Blend.

The Crossroads Inn at Pippin Hill

Since 1820, the The Crossroads Inn at Pippin Hill has been providing travelers a place to relax minutes from the University of Virginia. Guests here can enjoy panoramic views of the Blue Ridge mountains while choosing to stay in rooms, suites or the Summer Kitchen Cottage. Each room also has a private bathroom and individually-controlled air conditioning.

As an added bonus, the Inn at Crossroads is in the Mid-Way Tasting Triangle, with ciderworks, vineyards, and wineries in all directions. The closest one is Pippin Hill Farm & Vineyards, just a short three-minute walk from the Inn.

Glass House Winery Bed & Breakfast

Glass House Winery features a unique tropical greenhouse for tasting delicious wines and offers a bed & breakfast. With three bedrooms downstairs and a two-bedroom suite upstairs, there are plenty of options to enjoy a charming and relaxing night overlooking the vineyard, the winery, and the Blue Ridge Mountains in the distance. Or, bring the whole family or a group of friends to rent out the entire house for a private weekend full of wine and fun!

The Inn at Stinson Vineyards

The Inn at Stinson Vineyards is a modern take on the timeless country bed & breakfast. They offer four suites, and each of them allows guests to marvel at the breathtaking views of the vineyard. They all also have ensuite bathrooms, King-sized beds, and other modern amenities, ensuring the utmost comfort of those who choose to stay there.

Guests will feel like they are living in luxury during every stay with daily three-course breakfasts, wine-paired dinners in the Wine Cellar, and the chance to admire the majestic mountain views from the comfort of the heated pool or outdoor patio.

Lake House at Chisholm Vineyards

Situated on 500 acres at Adventure Farm, Chisholm Vineyards aims to make the best wines that are true to the terroir. There is also live music and a food truck from mid-March through October, as well as additional pop-up events throughout the year. In their tasting room, Chisholm Vineyards offers twelve small-lot, award winning, and fully estate grown wines for visitors to try.

For guests looking to stay on the property, the Lake House at Chisholm Vineyards provides a farm stay experience for groups up to 12 people that put you near Charlottesville, but in a private and peaceful setting.

Mount Ida Reserve Getaway Stays

Mount Ida Reserve Getaway Stays has long term and weekend rentals on Mount Ida Reserve’s 5,000 acres. Guests can choose from quaint cottages, brick Georgian’s, and historic manor home accommodations during their stay, all with access to Mount Ida’s private lake for fishing, kayaking, or relaxing moments on the beach.

The Tasting Room and Taphouse, also located on the reserve, offers both onsite vineyards and a brewery. In addition, their wines and craft beers are excellently paired with a seasonal menu made of the finest ingredients from local farms and food artisans.

The Villa at Hazy Mountain

The Villa is the original structure of the Hazy Mountain Estate, a charming manor that sleeps 14 and can be rented for a full week with a minimum stay of 3 nights. The elegant furnishings and historic decor offer the charm of an Italian Villa with all of the convenience expected of a premier stay.

The delightful Villa is located within steps of Hazy Mountain Vineyards & Brewery.

Vineyard Stays

In addition to the above winery lodging, these local accommodations have vineyards on-site. Slip into the comfort of these quaint properties, enjoy the vineyard views, and take an easy drive to tasting rooms at neighboring wineries.

Arcady Vineyard Bed & Breakfast

Arcady Vineyard Bed & Breakfast offers 14 acres of serenity, situated approximately 5 miles from downtown Charlottesville. In addition to gorgeous views of the vineyard and surrounding landscape, guests who stay at the bed & breakfast located on the property will be treated to a wine fridge stocked with a bottle of sparkling wine, a glass of local wine on check-in day, farm-fresh wine country breakfasts, and a back deck perfect for lounging out and watching the wildlife!

Meriwether Springs

Situated on 40 acres with 2 ponds, a 3-acre lake, and the beautiful Ivy Creek, this winery estate is home to a 4 bedroom, 3 bathroom house which sleeps up to 14 people, offering a secluded, expansive and quiet retreat, that is only minutes from Charlottesville's historic Downtown Mall! This beautiful spacious building overlooks the vineyard and provides a perfect choice for your sip & stay vacation.

Woodville Bed & Breakfast

Located in the rural historic area of Southern Albemarle County, Woodville Bed & Breakfast offers a perfect place to relax and enjoy history without leaving behind the comforts of the 21st century.

Spend your days exploring the areas many attractions, lounge by the pool, or sit back and simply enjoy the view. Guests over age 21 are invited to a complimentary wine tasting produced with grapes grown on the Woodville farm property.

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