Places to Stay

A Historic St. Michaels Vacation

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.

  • 703-732-2075
  • St. Michaels 21663

Aida’s Victoriana Inn

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.

  • 410-745-3368
  • St. Michaels, MD 21663
Bartlett Pear Inn store front.

Bartlett Pear Inn

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.

  • 410-770-3300
  • Easton, MD 21601

Bay Cottage

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

  • 410-745-9369
  • St. Michaels, MD 21663

Best Western Plus Easton Inn & Suites

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.

  • 410-822-7100
  • Easton, MD 21601

Bishop’s House Bed and Breakfast

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

  • 410-820-7290 or 800-223-7290
  • Easton, MD 21601
Black Walnut Point Inn on Tilghman Island in Talbot County, Maryland

Black Walnut Point Inn

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.

  • 410-886-2452
  • Tilghman Island, MD 21671

Captains Watch Vacation Cottage

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

  • 410-886-2643
  • Tilghman Island, MD 21671

Cherry Street Inn

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.

  • 410-745-6309
  • St. Michaels, MD 21663

Combsberry Inn

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.

  • 410-226-5353
  • Oxford, MD 21654
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