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


Bay Cottage warmly welcomes you to our picturesque St. Michaels, Maryland Waterfront Retreat. We are on a point of land with a 500 foot shoreline situated on the Eastern Shore of the Chesapeake Bay. This ideal location affords Bay Cottage the luxury of enjoying a cozy, private, quiet waterfront location, while just minutes away from the heart of St. Michaels, where there are shops, restaurants, museums, markets, golf course, and parks to be enjoyed at your leisure. This makes Bay Cottage 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, and those just looking for rest and relaxation, 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

Go! Fly Away. “Flyer” on Newport-Bermuda Race 2014

Flyer, sail # 2213, skippered by Doug Abbott of Bay Cottage, St. Michaels, Maryland will start the Newport-Bermuda Race tomorrow (June 20, 2014).  Let us Root for our team!

To Mom, with love – Mother’s Day 2014


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

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.