• 3 Lighted Har-Tru Tennis Courts

  • Waterfront Resort with Yacht Club

  • Pete Dye Golf Course

  • Sailing School

  • Spa & Fitness Center

  • Outdoor Pool


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.



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.

"The Inn at Perry Cabin has three terrific tennis courts with lights that dry in an instance, and a truly wonderful tennis program and tennis instructor. I played the number one position my sophomore junior and senior years on my high school team that was undefeated over eight years,. I won the State Championship my senior year, and was a tennis instructor myself during my college years. I say this to give background to the fact that I know what it takes to have a good tennis program, and the Inn at Perry Cabin has such a program"

- C.S., Tennis Resorts Online review


308 Watkins Ln
St. Michaels, MD 21663


  • Adult Tennis Programs

  • Junior Tennis Programs

  • Special Events

  • Tennis Camps

  • Tournaments

  • Leagues


Cliff Drysdale Tennis

625 Mission Valley Rd
New Braunfels, TX 78132

(830) 625-5911 

© 2020 by Cliff Drysdale Management, A Troon Company