Inns in & Around Charlottesville

The Hollymead House exterior

Want to stay somewhere slightly less conventional but still enjoy a relaxed setting, fine coffee, and turn-down service? Think about staying in one of a dozen boutique inns in or around Charlottesville.  Our recommendations below emphasize stylish settings for your stay, but two other details are key: location and price. Do you want to be in-town or on the perimeter? What about price? Are you splurging or trying to be economical? Nail those considerations first, because when it comes to style, Charlottesville has no vacancy! Below is our list of compelling boutique hotels by location — In Town v. “Around” (i.e. Outside Town). Any one of these can deliver elegant accommodations and hospitality. Pricing varies with seasonality. Be sure to inquire ahead. Each recommendation is a springboard to launch you on a Charlottesville experience outside the ordinary.

In Town

South Street Inn

This stately manse recently re-opened and offers proximity to Charlottesville’s Downtown Mall. Suspend your disbelief, however, and return to yesteryear: The South Street Inn stands sentinel above Charlottesville’s Downtown Mall. It offers simple elegance in 24 guest rooms, relaxing interior common areas, and a wrap-around veranda. Best of all, it offers unmatched proximity to some of downtown’s hottest attractions, from cocktails to culture to fine dining and entertainment.

Dinsmore House

Named for Jefferson’s master carpenter, James Dinsmore, this 1820 brick peach across from the UVA Medical Center on West Main, is the real deal for a rustic, european-feel stay that puts you smack in the middle of town. From the original heart pine floors to the craft moldings above the doors, the inn’s nine guest rooms offer a labyrinth of history and travel sophistication that’s perfect for small groups. Check-in at street level couldn’t be more relaxed as the main corridor bustles with waiters and patrons jockeying for tables served by the inn’s acclaimed Farm Bell Kitchen, open from 8am-2pm. 24″ original brick walls insure quiet and a tented terrace in the back seals-in privacy. On-site parking and breakfast for two included.

The Inn at Court Square

The Innkeeper is Candace DeLoach, and the primary structure is the Butler-Norris House, circa 1785. The Inn offers 12 guest rooms in two adjoining houses.  Quietly tucked away along Charlottesville’s historic Court Square district just two blocks from the downtown mall, the inn is in the eye of Charlottesville’s cultural hurricane. The interior is extravagantly eclectic with innumerable period chandeliers, lanterns, pictures, and rugs. After all, the innkeeper is an interior designer! The ambiance is quiet and reserved. The hallways creak. Sh-sh. Breakfast is served daily for guests. 

Oakhurst Inn

35 hotel rooms and several cottages and houses constitute the offerings of the Oakhurst Inn. Since 2010, this “beach front” property, albeit on the backside of UVA’s Central Grounds, has transformed a small neighborhood and put the guest in the center of the student residential experience. Friendly staff, a chic bar and social spaces with occasional jazz, a swimming pool, and dining room serving breakfast and lunch are a few of the things that make a stay here unlike any other.


Around (or Outside of) Town

Clifton Inn

Situated 5 miles east of Charlottesville in the historic area known as Shadwell, The Clifton is a classic and unique Virginia country property. Thomas Jefferson’s son-in-law originally built it in 1799. Today the property encompasses a central Manor House surrounded by numerous cottages, extensive gardens, a delightful pool, and trails on 100 acres. The Clifton offers 7 rooms in the Manor House and 13 in surrounding cottages. The Clifton offers amazing concierge services that can save you time and enhance your overall stay. It has become a much sought-after wedding venue. Like its style and the luxury its guests enjoy, Clifton’s price point is at the top. Their splendid restaurant, 1799, is led by Michelin Starred Chef Matthew Bousquet and serves in an elegant library setting or private Wine Cellar. Or you can dine along an outdoor patio beside an elegant central bar. Clifton’s deep wine inventory ensures that you’ll find the perfect pairing.

Hollymead House

Recently acquired by UVA alumna Pam Calary and husband William, Hollymead House is one of the few guesthouse experiences on Charlottesville’s near north side. The Calarys spent 5 years painstakingly restoring this historic, and encroached, property. Six miles up 29-North from John Paul Jones Arena, the inn is surrounded by mature landscape that provides privacy and a peaceful oasis apart from nearby neighborhoods. When you park and enter Hollymead House’s front door, you enter into an earlier, southern-lier period. This old house becomes your own as its floors creak from one antiquated room to another, each lavishly decorated with antique prints, rugs, furniture, and lamps. The inn has a cozy British-style pub, and a sun-filled breakfast room, ensuring both breakfast and a nightcap will bookend a perfect day. Two guest rooms in the main house and four more in an adjoining wing make Hollymead House a fine destination for small-to-medium size groups who want an uncommon Charlottesville experience. The Inn is 2.5 miles from the airport.

Inn at Willow Grove

Ranked #1 Inn in the South by Travel & Leisure, this beautifully restored 1770’s plantation house with soaring columns, fine dining and cocktails, pool, spa, and stately grounds is only a stone’s throw from Woodberry Forest School and the historic town of Orange. Willow Grove is an extravagant option if you’re coming from the north on your way to Charlottesville, or if you want to be in the countryside close to Montpelier. The inn offers 4 guest rooms in the main house and 21 additional rooms in nearby cottages sprinkled throughout the elegant grounds. A fabulous downstairs restaurant and bar as well as a full-service spa complete an exceptional getaway destination. 

For our complete Charlottesville GUIDE to hotels click HERE.