Top 7 Historic Hotels In Charlottesville, Virginia - Updated 2024

1. Dinsmore Boutique Inn (from USD 191)

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While Dinsmore Boutique Inn is new in the hospitality business—its operation started only in the early 21st century—its history goes far back. Its name is a nod to its architect and carpenter James Dinsmore, who also built U.S. President James Madison’s former residence, Montpelier, in 1809.

In the early 19th century, while working on the University of Virginia’s architecture, Dinsmore also made Dinsmore Inn’s townhouse his project. The original facade is designed with red brick that resembles the university’s Rotunda. Today, the property features nine elegant guest rooms and an in-house restaurant serving new-Southern cuisine.

2. Inn at Court Square (from USD 439)

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With a city as rich in history as Charlottesville, you deserve accommodation that is just as meaningful. Inn at Court Square occupies a pair of homes in the city’s downtown area. One dates back to 1785, while the other is from the early 20th century. Guests can admire Federal-style architecture and enjoy proximity to shopping, dining, and entertainment establishments.

Each room in Inn at Court Square is designed with beautiful furnishings, including vibrant walls, chandeliers, and antique decors.

Nearby historic hotels

3. Inn At Willow Grove

Editor's Note: Photo taken from the establishment's official social account

Nestled in Virginia’s dreamy Wine Country, Inn At Willow Grove is a 40-acre (16-hectare) property with a sophisticated reformed plantation house for a centerpiece. With the Blue Ridge Mountains for a next-door neighbor, guests are treated to mesmerizing scenery throughout their stay.

Inn At Willow Grove’s builders was the same ones who built the University of Virginia, picked by the US president Thomas Jefferson. Neoclassical architecture with an American flair were utilized to fashion the property in 1778. Before its sale to the present-day owners in 2008 and the succeeding renovation, the inn served as a bed and breakfast for over two decades.

Inn At Willow Grove

Address: 14079 Plantation Way, Orange, VA 22960, United States

Star Rating: 3 Star

Travelers Review: Excellent 4.6(from 241 reviews)

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4. Boar's Head Resort (from USD 291)

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For vacationers longing for a serene and scenic countryside retreat, Boar’s Head Resort is the perfect home base for you. This 4-star property sits on 600 acres (243 hectares) of land belonging to the state’s first land grant in the first half of the 18th-century. In 1759, a retreat called Terrell’s Ordinary started operation on the same place where the present-day Boar’s Head Resort sits.

After many ownership changes, Boar’s Head Resort formally opened in the late 1900s. From its 54-room start, it thrived and expanded to offer 168 guest rooms. On-site dining, sports facilities, and spa services are in store for guests.

5. Prospect Hill Inn & Restaurant (from USD 217)

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Prospect Hill Inn & Restaurant is only 15 minutes away from the hustle and bustle of Charlottesville. It showcases frame-house, country-style aesthetics and offers tastefully curated rooms and cottages with a history that spans back to 1699. Some of the accommodations were built in 1870, categorizing them as the newer ones. Complimentary WiFi and fireplaces await.

Vacationers can kick-start their days with gourmet breakfasts and cap it off with fine dining. From scenic walks to bonfires, you have plenty of things to try within the property.

6. Hotel 24 South (from USD 109)

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Hotel 24 South is a 1924 hotel included in The Historic Hotels of America. It features Colonial Revival architecture and a beautiful brick facade, which impressed Shenandoah Valley social butterflies at the time.

This 3-star hotel, while seemingly quaint on the outside, boasts modern-day facilities inside. It houses a swimming pool, a hot tub, fitness center, and posh function rooms. Accommodations here come with free WiFi, delighting travelers.

7. The Blackburn Inn (from USD 133)

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Nestled in The National Register of Historic Places’ Western State Hospital, The Blackburn Inn is part of a massive historic complex and was once an office for the hospital. While the structure was built in the 1830s, it was only in 2018 that it was introduced to the world as The Blackburn Inn. The name is a nod to its architect, James Blackburn, Thomas Jefferson’s protege.

Today, this property offers classy accommodations and an art gallery that showcases regional talents.

Dive into Charlottesville's rich history and culture

Charlottesville is a charming city with a rich history. Many iconic structures here are related to the works of the US president Thomas Jefferson, including the University of Virginia itself. More so, you’ll find plenty of historic hotels in and out of the city, which delight history and culture enthusiasts.