Places to Stay

Sunset Cottage

The Sunset Cottage is a working class Waterman’s Cottage (circa 1790-1805).

  • 410-745-2929
  • St. Michaels, MD 21663

Tarr House Bed & Breakfast

The Inn stands on the north side of Green Street, the center of historic St. Michaels, overlooking the St. Michaels Harbor and the Church Cove park. This ideal water location affords breathtaking views and within short walking distances to shops, restaurants & museums.

  • 410-745-2175
  • St. Michaels, MD 21663

The Inn at Perry Cabin

Once a private estate named after Commodore Oliver Hazard Perry, The Inn at Perry Cabin is an elegant circa 1816 property located on 25 breathtaking acres overlooking the Miles River, a tributary of the Chesapeake Bay and is a short stroll from the historic town of St. Michaels, Maryland.

  • 410-745-2200
  • St. Michaels, MD 21663
Oaks Waterfront Inn Building Front

The Oaks Waterfront Inn & Events

Our historic luxury waterfront inn that specializes in weddings and conferences is located between St. Michaels and Easton. On-site catering is offered by Chef Paul Milne, previous owner of the highly acclaimed 208 Talbot.

  • 410-745-5053
  • Royal Oak, MD 21662

The Snuggery Bed & Breakfast

Located in historic St. Michaels, Maryland, the Snuggery is our town’s oldest residence. Restored and fully modernized, the Snuggery today is our home, antiques and all, and a place we love our guests to share and enjoy with us. Thus, a stay at the Snuggery has a special advantage. We offer you the opportunity for both an historic and a residential Bed and Breakfast experience.

  • 410-745-2800
  • St. Michaels, MD 21663
Harbour Inn Viewed Across Harbour.

The Tidewater Inn

A luxurious retreat located just outside of Baltimore, Washington, D.C .and Wilmington, the Tidewater Inn is appointed with modern comforts, state-of-the-art conference space and exquisite banquet rooms ideal for weddings and special events. The Inn features 95 well-appointed boutique guest rooms, a tavern-style restaurant and banquet rooms.

  • 410-822-1300
  • Easton, MD 21601

Tidewater Vacations

Tidewater Vacations has taken “vacation rental homes” to the next level.

Offering full concierge service while you are staying in one of our waterfront vacation rental homes, which are located near St. Michaels, in Talbot County on the Eastern Shore of the Chesapeake Bay.

  • 443-786-7220 or 410-745-5255
  • St. Michaels, MD 21663

Tidewater Weddings

Welcome to the Eastern Shore’s premier waterfront wedding venue. Kirkland Manor, a private estate located between Easton and St Michaels which can accommodate up to 400 for your special day.

  • 410 745 5255
  • St. Michaels, MD 21663

Wades Point Inn on the Bay

A true “jewel of the Chesapeake Bay,” the historic Wades Point Inn and farm is a place where the stress of the world washes away. Located minutes from St. Michaels on the Chesapeake Bay, Maryland Eastern Shore, our inn is an easy getaway from Washington D.C., Baltimore and Philadelphia.

  • 410-745-2500
  • McDaniel, MD 21647