Map & Directions 410-745-9369 24640 Yacht Club Road, St. Michaels, MD 21663


Bay Cottage warmly welcomes you to picturesque St. Michaels, Maryland. Located less than one mile from town, on a point of land with waterways on three sides providing a 500-foot private, relaxing riverbank environment.

This ideal location situated on the Eastern Shore of the Chesapeake affords Bay Cottage the luxury of enjoying a cozy, private, quiet waterfront location down our long and peaceful private tree-lined driveway, 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. Whether you are – the outdoorsman, the sailor, the sportsman, the foodie, the nature lover, the history buff, the artist, the poet, the yogi, or those fun loving people just looking to get away for rest and relaxation, our warmest hospitality and finest services await you.


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 in every room 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 local farms, gardens, and the Chesapeake Bay. Chef Jackie’s innovative cuisine blends Chesapeake heritage with sophisticated Asian and French cooking techniques. Join us for the three-course full breakfast served on the waterside porch when you book a Bed & Breakfast stay. More


Imagine lounging comfortably on our point of land or the pier where classic yachts are docked. Watch kayaks, egrets and herons glide through the water. Take a refreshing dip in the pool, rinse off at the outside shower, relax in the teak chaise lounge, or settle into a hammock and watch the yachts sail by. Reward yourself with a cabana or spa massage. When the weather cools down, settle into an Adirondack chair by the waterside fire pit, roast some marshmallows and relax. More


Enjoy sports and outdoor activities – crab off the dock, fish off the pier, sail away into the sunset, kayak into St. Michaels, bike / walk / jog through parks and nature trials, dip into the pool, play a round of golf, take a yoga class, go wine tasting, brewery hopping, or just relax and do nothing –like take a nap in the waterside hammock. Play. Enjoy. Relax. Speaking of relaxing, Bay Cottage has many amenities for a most memorable time. More


Bay Cottage was built and enjoyed as a sailing, fishing, and hunting retreat on the Chesapeake Bay. We have retained these unique and historic elements to preserve this heritage. The interior design was inspired by our bayside surroundings by incorporating everything from the classic and racing yachts at our harbor to the quintessential Chesapeake way of life. Our interior reflects and celebrates the colors and themes of a Chesapeake Bay sunlit day. More


Inspired by the water surroundings, we integrated our pool, docks, harbor, pier deck, poolside cabanas, outdoor shower, soaking tub and waterside spa into a light-filled, fresh, and open sanctuary. Our spa offers a nurturing Chesapeake Bay retreat to celebrate the restorative power of nature. Come and relax your body, revitalize your mind, and renew your spirit. Our spa services are exclusive to Bay Cottage guests. 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.

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

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