Map & Directions 410.745.9369 24640 Yacht Club Road, St. Michaels, MD 21663


Bay Cottage warmly welcome you to our picturesque St. Michaels, Maryland Waterfront Vacation Retreat.  We are on a point of land with 500’ shoreline on the Eastern Shore of Chesapeake Bay. A short walk to the shops, restaurants, museums, markets, golf course, and parks, yet private and quiet, Bay Cottage is ideal for your Chesapeake Bay vacation.  With great honor, we offer you – the outdoorsman, the sailor, the sportsman, the foodie, the environmentalist, the history buff, the artist, the poet, the yogi, the layabout, our warmest hospitality and finest services.


Blending tradition, comfort, elegancy, and refinement, each Bay Cottage room is carefully renovated, individually styled, and classically decorated. On a point of land, every window offers water views. Book a room for your B&B romantic getaway or take the whole house as your Vacation Rental Home. More


Savor the harvest from our Farm & Culinary Gardens. Chef Jackie’s innovative cuisine blends Chesapeake heritage with sophisticated Asian and French cooking techniques.  We honor Farm-to-Table, Sustainable Farming, and Fair-Trade practices. More


Crab off the dock, fish off the point, sail down the river, kayak into town, bike through parks, dip into the pool, play a round of golf, take a yoga class, go wine tasting, or just do nothing – take a nap in the hammock.  Play. Enjoy. Relax. More

Recent News & Events

Me, sailor


Eastern Sunday, 1995, a cold and windy day on the Chesapeake Bay water. I was sailing a Womanship boat with 7 women, 2 of them sailing instructors, into Annapolis Harbor. The sky was blue and clear, the air was clean and crispy, and the water cold and choppy. Annapolis is a beautiful port to come into. In the background, the Bay Bridge, with its imposing… Read More

Kayaking into St. Michaels, MD


I believe we were all born with a unique talent. Some can cook, become chefs, and got TV shows like Hell’s Kitchen. Some can write and wrote “Harry Potter” books. Some can sing and sold millions of Beatles albums. Some can direct and made “Titanic” and “Avatar”. A county music star, who said he is not good at anything “but I am pretty good at… Read More

My 3 wishes


John F. Kennedy said: “When I was growing up I had three wishes. I wanted to be a Lindbergh-type hero, learn Chinese, and become a member of The Algonquin Round Table”. His 3 wishes are very close to my 3 wishes when I was growing up in the 50’s and 60’s in poverty-stricken Taiwan. To be a Lindbergh-type hero was the only thing I wanted… Read More

Set Sail


After a major loss, how do we bounce back? How can we be the person we always wanted to be? Here is what my beloved Kripalu yoga teacher Jovinna Chan, who is the one in this beautiful picture, taught me: Be yourself. Be brave. Focus on what’s important in life. Move on. Enjoy.

Special Offers


Create your bespoke journey in ‘the heart & soul of the Chesapeake Bay’ by choosing from our wide selections of add-on enhancements; from water sports, yoga, harvesting the Bay, farm tours to Arts & Cultures. Enjoy our intimate and personalized service.

Offer Details

Hot Deals


Get the best and greatest deals and discounts you can find for your waterfront vacation.

Special Deals



Local Attractions


The historic village of St. Michaels is just a short walk or kayak ride from Bay Cottage. St. Michaels is a lovely Chesapeake Bay town with a harbor – well known for its fine  B&B’s, shops, restaurants, winery, brewery, distillery, and museums.


The Chesapeake Bay Maritime Museum is the perfect place to learn about the history, lifestyle, culture, and people of the Bay.  CBMU offers lots of learning and children’s programs.



Sailing, kayaking, canoeing, fishing, chartering on the ever-changing, ever-fascinating waters of Chesapeake Bay offers you the most memorable time and will draw you back again and again.