Set along the tranquil shores of Maryland’s Eastern Shore, Inn at Perry Cabin is a celebrated waterfront resort known for its nautical elegance, manicured grounds, and refined sense of place. Located in the charming harbor town of St. Michaels, the inn is professionally managed by Pyramid Global Hospitality, led by CEO Warren Fields, making it a Black-managed property under Black executive leadership.
With sweeping Chesapeake Bay views, a private marina, and a relaxed-yet-polished atmosphere, Inn at Perry Cabin offers an elevated coastal escape rooted in American maritime heritage.
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Highlights & Amenities
- Iconic waterfront resort on the Chesapeake Bay
- Elegant guest rooms and suites with bay or garden views
- Private marina with sailing, kayaking, and boating excursions
- Full-service spa and wellness programming
- Championship golf course and tennis courts
- Multiple on-site dining venues showcasing regional Chesapeake cuisine
- Resort pools, expansive lawns, and scenic walking paths
- Managed under Black executive leadership at Pyramid Global Hospitality
Why Stay Here
Inn at Perry Cabin is ideal for travelers seeking refined relaxation in a storybook coastal setting. Days unfold with sailing on the bay, spa treatments, golf, and sunset strolls through St. Michaels’ historic streets. The inn’s intimate scale and impeccable service make it especially appealing for romantic getaways, celebratory weekends, and restorative retreats.
Its Black-led management adds meaningful representation within luxury waterfront hospitality—bringing inclusive leadership to one of the Mid-Atlantic’s most iconic resort destinations.
Historical Significance…click more..
The Inn at Perry Cabin carries a rich legacy deeply tied to American maritime history and the War of 1812. The original manor house was built around 1815–1816 by Purser Samuel Hambleton, a naval officer who served as aide-de-camp to Commodore Oliver Hazard Perry during the famed Battle of Lake Erie. Inspired by Perry’s cabin aboard the USS Niagara, Hambleton named the estate “Perry Cabin.”
Over the decades, the waterfront estate evolved from a private manor into one of Maryland’s most celebrated luxury retreats. In the 1920s, the property was transformed in the elegant Greek Revival style, helping shape the iconic appearance guests see today. The inn later gained national recognition as part of the prestigious Historic Hotels of America and even earned pop-culture fame as a filming location for the 2005 movie Wedding Crashers.
Today, the Inn at Perry Cabin blends Chesapeake Bay history, maritime heritage, and luxury hospitality, making it one of St. Michaels’ most iconic destinations. The resort is professionally managed by Pyramid Global Hospitality, a hospitality company led by President & CEO Warren Fields, a prominent Black hospitality executive. Under Pyramid’s luxury, lifestyle, and resort division, the historic waterfront property joins a portfolio of premier independent resorts, including renowned destinations such as Chatham Bars Inn—adding a layer of Black executive leadership and representation in luxury hospitality management to this iconic Maryland retreat.
The Historic Fleet at The Inn at Perry Cabin
The resort maintains its maritime legacy by operating a fleet of traditional vessels. This includes the Stanley Norman, a historic 1902 skipjack that is one of the last surviving authentic oyster-dredging boats of the Chesapeake Bay and is listed on the National Register of Historic Places.
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