St. Michaels

  • Shopping – Boutique Shopping in Historic District
  • Restaurants – Ranges from fine dining to crab houses
  • Groceries – Several Major and Gourmet Stores

Community Information

During the War of 1812, St. Michaels gained its name as “the town that fooled the British”. The residents of St. Michaels, having been forewarned that British barges were positioned on the waters to attack with cannon fire, hoisted lanterns into the trees above the city. The first successful “blackout” fooled the British into overshooting the town’s houses and shipyards. Only one house, forever since known and Cannonball House, was struck. The industry was largely concentrated around shipbuilding and seafood packing, and there are several museums and cultural centers that nod to this heritage. However, today St. Michaels enjoys primarily a healthy tourism industry as guests come from far and near to enjoy all the wonderful things this charming town has to offer. Many will also recognize St. Michaels as the backdrop of several popular movies, including “The Wedding Crashers”.

Upscale Shopping, Historical Interest, Chesapeake Bay Maritime Museum, Waterfront Crab Houses, Charters and Tours, Fine Dining Farmers Market, Community Pool (fee for use), Nearby Golf.

Browse Our St. Michaels Vacation Rentals Below

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Crabber's Cove

St. Michaels
Beds: 3 | Baths: 3 | Sleeps: 6
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Caulk's Cove

Bozman
Beds: 3 | Baths: 2.5 | Sleeps: 6
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Heron Point

Royal Oak
Beds: 4 | Baths: 2.5 | Sleeps: 8
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Emily's Lane

Wittman
Beds: 4 | Baths: 3.5 | Sleeps: 8
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Pines at Barrett Cove

Saint Michaels
Beds: 3 | Baths: 3 | Sleeps: 6
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Retreat on Grace Creek

Bozman
Beds: 6 | Baths: 8 | Sleeps: 12
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Graceful View

Bozman
Beds: 3 | Baths: 2 | Sleeps: 6
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Loblolly Cove

Neavitt
Beds: 4 | Baths: 3 | Sleeps: 8
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Escape Farm

Royal Oak
Beds: 3 | Baths: 4 | Sleeps: 6
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Bushey Heath Farm

Royal Oak
Beds: 4 | Baths: 2 | Sleeps: 8
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At Tricefields Court

Saint Michaels
Beds: 4 | Baths: 5 | Sleeps: 8
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Sunrise Cove

Saint Michaels
Beds: 4 | Baths: 3 | Sleeps: 8
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Pines at Irish Creek

Royal Oak
Beds: 4 | Baths: 3 | Sleeps: 8
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Duck Cove

Neavitt
Beds: 2 | Baths: 1 | Sleeps: 4
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The Water House

Easton
Beds: 5 | Baths: 5.5 | Sleeps: 9
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Osprey Point

Saint Michaels
Beds: 4 | Baths: 3.5 | Sleeps: 8
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Acorn Point

Easton
Beds: 5 | Baths: 5.5 | Sleeps: 10
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Mallard Point Cottage

McDaniel
Beds: 4 | Baths: 3 | Sleeps: 8
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Broadwater View

Royal Oak
Beds: 5 | Baths: 4.5 | Sleeps: 10
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PennyWhistle

McDaniel
Beds: 4 | Baths: 3 | Sleeps: 8
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The Landing

Saint Michaels
Beds: 4 | Baths: 3 | Sleeps: 8
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Captain's Cove

Saint Michaels
Beds: 5 | Baths: 4.5 | Sleeps: 10
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Carpenter Alley

St. Michaels
Beds: 3 | Baths: 3 | Sleeps: 6
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Town and Country

Saint Michaels
Beds: 4 | Baths: 3 | Sleeps: 10
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Chesapeake Pines

Easton
Beds: 4 | Baths: 4 | Sleeps: 8
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