USA: Inn at Perry Cabin, St. Michaels, Chesapeake Bay
A Chesapeake Bay Sailing Estate
Built in 1816 to resemble a naval commodore’s shipboard cabin, Inn at Perry Cabin sits on the Miles River in the heart of St. Michaels, on Maryland’s Eastern Shore. Sir Bernard Ashley of Laura Ashley expanded the property in the late 1980s, and Belmond’s ownership since 2014 has kept the 19th-century, colonial-inflected design intact across the hotel’s 79 rooms and suites, most with private balconies or terraces overlooking the water. It has been a member of Historic Hotels of America since 2018 and is instantly recognizable to film fans as the setting for the wedding reception scene in Wedding Crashers.
Dining centers on Sherwood’s Landing, where Chesapeake seafood and river views set the table for both casual and dressier nights. The Inn’s own Sailing Academy runs ASA-certified courses and chartered cruises aboard some of the best yachts on the Bay, while the Linden Spa balances things out with an infinity pool, seasonal treatments, and a stocked apothecary. There is no formal kids club, but the grounds, sailing programs, and easy access to antique shops and woodland trails make it a welcoming, unfussy base for family getaways as well as couples’ weekends.
Life at Inn at Perry Cabin
79 rooms and suites, most with private balconies or terraces on the water
Sherwood’s Landing restaurant for Chesapeake seafood and river views
A private Sailing Academy with ASA-certified courses and chartered cruises
Linden Spa with an infinity pool, seasonal treatments, and an apothecary
Manicured grounds, antique shopping, and woodland trails just outside the door
Why Inn at Perry Cabin, Why the Chesapeake
A genuine sailing destination with its own on-site academy and yacht fleet
Historic 1816 architecture and a real sense of place, not a generic waterfront resort
St. Michaels offers an easy, walkable small-town base with antique shops and seafood houses
An easy weekend drive from Washington, D.C., Baltimore, or Philadelphia without needing a flight
Ideal For: Sailing enthusiasts, history-minded couples, and families or groups wanting an easy, historic Chesapeake Bay escape within driving distance of the mid-Atlantic’s major cities.
Gold Coast Travel Perks
Unlock Virtuoso amenities when you book with Gold Coast Travel:
Complimentary daily breakfast
$100 resort credit, and an additional $100 credit for bookings in a Luxury Water View Suite
Early check-in / late check-out, subject to availability
Upgrade at check-in, subject to availability
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