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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Town and Country FROM $4900

Town and Country

Saint Michaels
Beds: 4 | Baths: 3 | Sleeps: 10
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Captain's Cove FROM $5625

Captain's Cove

Saint Michaels
Beds: 5 | Baths: 4.5 | Sleeps: 10
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Duck Cove FROM $1200

Duck Cove

Neavitt
Beds: 2 | Baths: 1 | Sleeps: 4
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PennyWhistle FROM $2750

PennyWhistle

McDaniel
Beds: 4 | Baths: 3 | Sleeps: 8
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Crabber's Cove FROM $2400 - $2750

Crabber's Cove

St. Michaels
Beds: 3 | Baths: 3 | Sleeps: 6
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Loblolly Cove FROM $4075

Loblolly Cove

Neavitt
Beds: 4 | Baths: 3 | Sleeps: 8
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Escape Farm FROM $3000

Escape Farm

Royal Oak
Beds: 3 | Baths: 4 | Sleeps: 6
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Broadwater View FROM $5800

Broadwater View

Royal Oak
Beds: 5 | Baths: 4.5 | Sleeps: 10
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Graceful View FROM $2450

Graceful View

Bozman
Beds: 3 | Baths: 2 | Sleeps: 6
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Pines at Irish Creek FROM $2720

Pines at Irish Creek

Royal Oak
Beds: 4 | Baths: 3 | Sleeps: 8
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Mallard Point Cottage FROM $2050

Mallard Point Cottage

McDaniel
Beds: 4 | Baths: 3 | Sleeps: 8
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Emily's Lane FROM $4500

Emily's Lane

Wittman
Beds: 4 | Baths: 3.5 | Sleeps: 10
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Chesapeake Pines FROM $2100

Chesapeake Pines

Easton
Beds: 4 | Baths: 4 | Sleeps: 8
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Heron Point FROM $4250

Heron Point

Royal Oak
Beds: 4 | Baths: 2.5 | Sleeps: 8
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Sunrise Cove FROM $3000

Sunrise Cove

Saint Michaels
Beds: 4 | Baths: 3 | Sleeps: 8
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Bushey Heath Farm FROM $3500

Bushey Heath Farm

Royal Oak
Beds: 4 | Baths: 2 | Sleeps: 8
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Caulk's Cove FROM $1890

Caulk's Cove

Bozman
Beds: 3 | Baths: 2.5 | Sleeps: 6
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Osprey Point FROM $3225

Osprey Point

Saint Michaels
Beds: 4 | Baths: 3.5 | Sleeps: 8
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At Tricefields Court FROM $4500

At Tricefields Court

Saint Michaels
Beds: 4 | Baths: 5 | Sleeps: 8
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Pines at Barrett Cove FROM $4025

Pines at Barrett Cove

Saint Michaels
Beds: 3 | Baths: 3 | Sleeps: 6
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Acorn Point FROM $8500

Acorn Point

Easton
Beds: 5 | Baths: 5.5 | Sleeps: 10
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Retreat on Grace Creek FROM $11000

Retreat on Grace Creek

Bozman
Beds: 6 | Baths: 8 | Sleeps: 12
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The Landing FROM $4000

The Landing

Saint Michaels
Beds: 4 | Baths: 3 | Sleeps: 8
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The Water House FROM $3500 - $4200

The Water House

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