Real Estate

Tidewater Vacations has taken “vacation rental homes” to the next level and are proud to present the “Hamptons of the Chesapeake Bay”.


Offering full concierge service while you are staying in one of our waterfront vacation rental homes, which are located near St. Michaels, in Talbot County on the Eastern Shore of the Chesapeake Bay.


We offer an inventory of holiday rental homes on a par with the luxury and comfort offered in the Hamptons. We are proud to invite you to enjoy the serenity, style and comfort in one of our exclusive waterfront homes – all of which have private pools, docks and some with tennis courts. View our Premiere Waterfront Estate Vacation Rentals

Make your getaway even more memorable! Hire your own  personal chef or have an authentic Eastern Shore Crab Feast!


St. Michaels, Maryland has been consistently voted as one of the BEST places to vacation! Interested in reading more? Just click here! New articles posted all the time!


We look forward to assisting in the planning of an unforgettable vacation for your family.

Southern Living Magazine ranks St. Michaels in the top 3 “Best Small Town Getaways”!

Our wonderful selection of 2 to 10 bedroom homes offer the perfect get-a-way for romantic couples, family vacations, reunions and weddings.

Weekend and weekly rentals available throughout the year. Our concierge team will help plan your vacation on the Eastern Shore from arranging for your own private chef, a rental boat, a visit to your luxury home by one of massage therapists to suggesting where to dine in the county. So relax, leave the planning of a memorable vacation to the people who care and know how to look after you!


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