Cliff Drysdale Tennis


Inn at Perry Cabin

St. Michaels, MD

Steeped in history and style, Inn at Perry Cabin is consistently ranked one of the best luxury resorts in the Mid-Atlantic, including #1 in the region by Condé Nast Traveler. The intimate resort, nestled along the Chesapeake Bay on Maryland’s Eastern Shore, boasts spectacular waterfront lawns and sweeping bay views, as well as a pristine fleet of sailboats and performance yachts, docked at the Inn’s private harbor.

The new Tennis Club includes three state-of-the-art outdoor Har-Tru tennis courts, lighted for both day and night play. Beginning this year, guests of the Inn will also have access to Links at Perry Cabin, the new 18-hole championship golf course designed by legendary architect Pete Dye. Additional guest amenities include the spa, full service fitness center, outdoor pool, sailing school and additional water activities.

The new tennis program will offer instructional options for all ages and levels including private and semi-private lessons, daily adult clinics, cardio tennis, beginner adult tennis, junior classes, seasonal camps and special events.



  • Adult Tennis Programs
  • Junior Tennis Programs
  • Special Events
  • Tennis Camps
  • Tournaments
  • Leagues
View Weekly Schedule
Director of Tennis

Andrew Reiley

Director of Tennis

A Long Island, New York native, Reiley played collegiate tennis at SUNY Oneonta before being selected for CDT's Professional Tennis U program. He has extensive experience with resort tennis management and programming.

Contact Andrew Reiley

Location Info

308 Watkins Ln
St. Michaels, MD 21663

Director of Tennis: Andrew Reiley

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