Change is in the air! Be on the lookout for our new, improved website featuring a virtual concierge, better visitor information and all the great features we currently have on-line. We are also offering a reduced 1/3 deposit rather than the traditional 50% deposit. Don't let another season pass you by!

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THE EASTERN SHORE — No longer a stop — a destination!

Always wondered what the Chesapeake Bay area has to offer? With over six hundred miles of waterfront, St. Michaels, MD is fast becoming a premier waterfront vacation destination. Most renowned as a fishing village, today’s Eastern Shore of Maryland casts a much wider net of vacation opportunities!

Sailing, kayak tours, bicycling, fishing and crabbing, swimming, relaxing on your private pier, strolling through quaint historic villages, fabulous casual and elegant dining, boutique shopping and eclectic art galleries are just some of the delights awaiting you when you plan your vacation on Maryland’s Eastern Shore! Visit our guest services section for information on special events, personal catering, boat and bike rentals and our local links to help plan your vacation.

Eastern Shore Vacation Rentals has all you need to plan your waterfront vacation:


We invite you to browse through a sampling of some of the finest waterfront cottages, homes and estate rentals in St. Michaels and the surrounding areas. If this is your first visit to the Eastern Shore, please visit our Explore the Area section to see which area best suits your vacation needs. We will be happy to assist you in planning your vacation in the towns of Easton, Oxford, Tilghman Island, Cambridge, St. Michaels, and Chestertown.

Don't Let Another Season Pass You By!



Eastern Shore Vacation Rentals, LLC

28282 Saint Michaels Road
Easton, MD 21601
Office: 410-770-9093 Toll Free: 1-866-398-2722
info@easternshorevacations.com