The house and cottages of A Historic St. Michaels Vacation are a group of five fully restored houses of various sizes clustered around the harbor in the heart of St. Michaels. The houses are available year round and can be rented individually.

This 1875 Historic Bed & Breakfast on the harbor in the heart of St. Michaels is nestled on an acre of groundswhere guest can enjoy our tranquil harbor-side ambiance. We invite you to relax and unwind in our beautiful home.

Our 7-bedroom Boutique Inn has lovely and very comfortably appointed rooms, all with private baths (some with soaking tubs), WiFi, flat screens, cozy sitting nooks, delicious breakfast and 10% off in the restaurant.

Bay Cottage, St. Michaels offers a waterfront vacation retreat in the heart of Eastern Shore of Chesapeake Bay.

Comfortably designed and furnished, you are sure to be able to unwind and relax throughout your entire stay, from the lobby to the indoor pool to your guest room.

Circa 1880 in-town home, furnished in period style, offers guests the charm of a by-gone Victorian era with 21st Century comfort.

Located on a 58-acre bird sanctuary, this private estate has broad porches, rocking chairs and a pool nestled in six acres of gardens and lawn.

We offer a fully furnished, pet-friendly, two-bedroom waterfront vacation cottage with a full kitchen. Rent by the day, week or month.

The Cherry Street Inn provides warm hospitality combining traditional elegance with modern comforts. It is a lovely 1880’s Victorian home, located in the heart of St. Michaels, one block from the Navy Point harbor and the Maritime Museum.

Combsberry is a historic 1730 English Country Manor home complete with a Carriage House and Cottage. The 30 acre waterfront Inn is an exclusive lifestyle destination located on the outskirts of Oxford, near St. Michaels and Easton, MD. Combsberry is a picturesque drive from Washington, D.C. and less than two hours from Baltimore and Philadelphia.