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. This first successful "blackout" fooled the British into overshooting the town's houses and shipyards. Only one house, forever since known as 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

Community Vacation Homes


Starting at (USD)

$740.00

Talbot County
  • 6 Guests
  • 3 Bedrooms
  • 3 Baths
  • Code: Pines at Barrett Cove
  • Pets Allowed
View Rental
Starting at (USD)

$295.00

Talbot County
  • 6 Guests
  • 3 Bedrooms
  • 2 Baths
  • Code: Graceful View
  • Pets Allowed
View Rental
Starting at (USD)

$355.00

Talbot County
  • 7 Guests
  • 3 Bedrooms
  • 2.5 Baths
  • Code: Caulks Cove
  • Pets Allowed
View Rental
Starting at (USD)

$595.00

Talbot County
  • 6 Guests
  • 3 Bedrooms
  • 3 Baths
  • Code: Swans Rest
  • Pets Allowed
View Rental
Starting at (USD)

$470.00

Talbot County
  • 6 Guests
  • 3 Bedrooms
  • 3 Baths
  • Code: Crabbers Cove
  • Pets Allowed
View Rental
Starting at (USD)

$630.00

Talbot County
  • 8 Guests
  • 4 Bedrooms
  • 4 Baths
  • Code: Cedar Cove on the Miles
View Rental
Starting at (USD)

$735.00

Talbot County
  • 8 Guests
  • 4 Bedrooms
  • 3 Baths
  • Code: Loblolly Cove
View Rental
Starting at (USD)

$645.00

Talbot County
  • 8 Guests
  • 4 Bedrooms
  • 3 Baths
  • Code: Thistle Dew
  • Pets Allowed
View Rental
Starting at (USD)

$590.00

Talbot County
  • 8 Guests
  • 4 Bedrooms
  • 3.5 Baths
  • Code: Osprey Point
  • Pets Allowed
View Rental
Starting at (USD)

$455.00

Talbot County
  • 8 Guests
  • 4 Bedrooms
  • 4 Baths
  • Code: Chesapeake Pines
  • Pets Allowed
View Rental
Starting at (USD)

$585.00

Talbot County
  • 8 Guests
  • 4 Bedrooms
  • 3 Baths
  • Code: Sunrise Cove
  • Pets Allowed
View Rental
Starting at (USD)

$620.00

Talbot County
  • 8 Guests
  • 4 Bedrooms
  • 3 Baths
  • Code: Mallards Landing
  • Pets Allowed
View Rental
Starting at (USD)

$600.00

Talbot County
  • 8 Guests
  • 4 Bedrooms
  • 2 Baths
  • Code: Bushey Heath Farm
  • Pets Allowed
View Rental
Starting at (USD)

$430.00

Talbot County
  • 8 Guests
  • 4 Bedrooms
  • 3 Baths
  • Code: Mallard Point Cottage
  • Pets Allowed
View Rental
Starting at (USD)

$770.00

Talbot County
  • 8 Guests
  • 4 Bedrooms
  • 2.5 Baths
  • Code: Heron Point
  • Pets Allowed
View Rental
Starting at (USD)

$980.00

Talbot County
  • 10 Guests
  • 5 Bedrooms
  • 4.5 Baths
  • Code: Captains Cove
View Rental