This Charming New Boutique Hotel Is Annapolis’ Best-Kept Secret

It’s difficult to have a bad time in Annapolis, Maryland. But it’s impossible to have a bad time in Annapolis if you’re staying at 86 State Circle, the latest luxury boutique hotel in one of America’s most historic cities. Located in a renovated townhouse in one of Annapolis’ two circles (aptly named Church Circle and State Circle to reflect the nation’s longstanding separation of church and state principle), this beautiful nine-room property is both a loving tribute to Annapolis’ past and a testament to its growing reputation as a luxury destination. 

The charm of 86 State Circle is evident before you even step foot onto the property, originally built in 1878 by Maryland’s then Attorney General. The impressive red brick façade, combined with fish-scale siding, is distinctive even within a neighborhood known for its venerable architecture. If you’re driving yourself (Annapolis is, after all, just shy of four hours from New York City and less than an hour from Washington, D.C.), the team will happily valet your car, especially given that Annapolis is infinitely walkable.

Come up a set of brick steps onto a veranda, and enter 86 State Circle through a set of double glass doors (pay attention to the lock detail, which is all original and carefully restored to its original gleam and glamour). You won’t find a traditional lobby in this hotel—instead, the team has carefully curated an experience to help you feel as though you’re an old friend staying in a familiar room. As such, check-in takes place in the hotel’s parlor, where comfortable couches, large easy chairs, and a beautiful antique leather-topped table also reside. This lobby, make no mistake, is meant to be enjoyed rather than traversed. 

While the parlor and adjacent dining room draw inspiration from London’s iconic Mayfair District, with a distinct focus on light, furniture, and art, the team has taken great care to also infuse historic Annapolis elements. Blue and white color palettes throughout reflect the city’s rich nautical background, and carefully curated art pieces pay homage to classic mid-Atlantic scenery. 

These thoughtful design elements continue into each of the nine guestrooms, located across four floors of the property. Each room is named after an element of Maryland’s legacy, including Queen Anne and William Paca (one of our Founding Fathers), and maintains original architectural features. 

For example, you’ll find beautifully high ceilings, grand windows, period moldings, and wainscotting throughout. But don’t worry—the 86 State Circle team has also brought modern technology alongside this historical opulence, which means that all rooms also feature one-touch blackout blinds, heated bathroom floors, and plush bedding dressed in Italian linens. 

Thanks to the hotel’s central location, you’re mere steps away from everything that Annapolis has to offer—whether you’re in search of a private yacht charter, a tour of the U.S. Naval Academy, or looking to do some antique shopping in historic downtown, 86 State Circle serves as the ideal jumping off point. 

And when you’re done exploring the town, be sure to come back to the hotel’s exclusive, speakeasy-style lounge, The Black Pearl, for an after (or pre) dinner drink. This beautiful subterranean space is the perfect place to unwind over a cocktail, drawing inspiration from New York’s Polo Bar. Alternatively, if you need a pick-me-up, head to the dining room for a cup of espresso, available anytime during the day (though it comes with a tray of pastries during the morning hours). 

So, whether you’re visiting Annapolis for the first time or returning to your old stomping grounds, calling 86 State Circle your home away from home is undoubtedly the beginning of a memorable trip. 

Top Takeaways

‍Location: Annapolis, MD 

‍Rating: Five-Star

‍The Vibe: London’s Mayfair district meets the best of the Chesapeake 

Food + Drink: Start your day with coffee and pastries in the dining room, and later in the day, head downstairs to The Black Pearl for a cocktail

‍Amenities: Bar; concierge; valet parking

Our Favorite Thing About the Hotel: We love the intimate, familiar feel of the hotel’s common spaces, including the lobby and The Black Pearl. They’re the perfect place to take a call, read a book, or relax outside of your room. 

5 Nearby Attractions: Chesapeake Bay charters, U.S. Naval Academy, Banneker-Douglass-Tubman Museum, Crypt of John Paul Jones, William Paca House & Garden

Any Personal Neighborhood Recs? Take a short walk to Annapolis’ historic downtown and grab some ice cream before heading to Zachary’s Jewelers to design a piece of custom jewelry 

Rooms: 9 rooms 

Pricing: Rooms start at $300/night  

Closest Airport: Baltimore-Washington International Thurgood Marshall Airport (BWI)

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