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Inn at Perry Cabin
©Roger Cox

Inn at Perry Cabin

St. Michaels, Maryland

By Roger Cox, Editor

The Inn at Perry Cabin sits at anchor alongside Chesapeake Bay in St. Michaels on Maryland's Eastern Shore. Both the name and inspiration date to 1816, when a naval veteran of the War of 1812, Samuel Hambleton, built the original inn—now the north wing of the hotel—to resemble the Commodore's cabin on the USS Niagara, a cabin once occupied by Commodore Oliver Hazard Perry, for whom he was aide-de-camp. Over the years the property has gone through numerous transformations—private home, farm, riding stable—before finally emerging as an intimate luxury resort with 75 rooms and a wealth of amenities, among them a waterfront restaurant, a pub, an 18-hole Pete Dye golf course, a spa and fitness center, an outdoor pool, a marina with a fleet of yachts, and a handsome complex of three Har-Tru tennis courts managed the Cliff Drysdale Tennis.
The mainland approach to the inn is a brick-paved allee of linden trees leading to the main entrance and a low-rise cluster of gabled white-clapboard buildings set off by nautical blue shutters. As inviting as that corridor is, the more appropriate means of arrival, given the region's maritime history, is by boat across Chesapeake Bay, heaving to at the resort's marina. (On request, the resort will send one of its yachts to meet you in Annapolis.) Either way, once there, you don't really need a car: the shops, restaurants, and historic homes of St. Michaels are within easy walking—or biking—distance, as is the 18-acre waterfront campus of the Chesapeake Bay Maritime Museum, the Inn's next-door neighbor. the Inn's small footprint—25 acres landscaped with flowers, magnolias, cypress—means none of its distractions are very far away with one exception: the golf course, which can be reached by free shuttle. That's the charm of it. You can settle in here on the Eastern Shore, play tennis or golf or bocce, go sailing, explore the bay on a kayak, bike into town, or get a massage and never be far from your well-appointed room or a feast of local oysters or crab.

Tennis Features

Pro Shop: 667-226-2033

Small inns rarely make tennis a priority. Even those with a court or two offer little in the way of tennis services. The courts are there is you want to use them, and if you need a lesson they may be able to bring in a local pro, but that's as far as it goes. So it's heartening to find not only an attractively designed complex of three lighted Har-Tru courts at the Inn but also a full-time professional from Cliff Drysdale Tennis (CDT), in this case Rob Wright. Originally from Hertfordshire in the United Kingdom, Wright coached and played competitive tennis in Europe before joining CDT in 2016, variously working at Stratton Mountain Resort, Omni Amelia Island Plantation Resort, and Omni Rancho Las Palmas Resort & Spa before taking over at the Inn when the tennis debuted in June 2018. He offers daily clinics and private lessons, catering both to hotel guests and local members.
Courts & Fees. There are three lighted Har-Tru courts surrounded by white wooden fencing backdropped by lines of trees. A small pro shop abuts a tennis fitted out, like the courts, with teak furnishings. Court time: $20/hour for guests.


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Inn at Perry Cabin
308 Watkins Lane
St. Michaels, MD 21663
Toll-free: 888-805-8885
Web Link: Inn at Perry Cabin

Travel Essentials

Seasons. Year-round for the Inn, April-October for tennis.

General Tourist Information. For general information about travel within Maryland, visit the Visit Maryland website. For specific information about the St. Michaels region, visit the St. Michaels Maryland.