Great Oak Manor, Chestertown

Steeped in local lore, Great Oak Manor harbors a 1938 Georgian residence set on 15 bayfront acres in Kent County. Legend has it that in the 1950s, one of its former owners ran a club and illegal casino on site. Over the years, the manor’s guests have included the likes of Ernest Hemingway and JFK.

Today the property is a 12-room hotel, fresh from a 2024 makeover spearheaded by Annapolis-based Interior Concepts, Inc. “Our goal was to respect the traditional architecture while adding upscale amenities and boutique accommodations,” says designer Andrea Blamphin. All rooms and suites—including the cheerful Marmaduke—boast working fireplaces. A clubby library stocks books and games. Summer guests can loll on the hotel beach or tool around on Trek Cruisers. Rates from $399, including breakfast; greatoakmanor.com

1313 West, Annapolis

Opened last year, 1313 West inhabits a 19th-century farmhouse that bordered a horse-racing circuit back in the day. So it’s only fitting that the hotel’s seven rooms and suites are named for famous racehorses.

Andrea Blamphin and Megan Ligday of Interior Concepts, Inc., outfitted the interiors. “The inn reflects a classic Southern aesthetic with a gentle modern twist,” notes Ligday. “The suites and public spaces offer serene palettes and patterns that are both playful and classic.” Sherwin-Williams Homburg Gray envelops the Secretariat Suite (top, left), furnished with a modern four-poster bed and comfy couch. After a day sail or a stroll through Maryland’s quaint capital, guests can unwind on the wraparound porch or in The Jockey Club Lounge, the hotel’s private speakeasy. Rooms from $499. 1313west.com