St Michaels Harbor at Sunset

St. Michaels

The town of St. Michaels is rich in history, having gained the nickname of “the town that fooled the British” during the War of 1812. Today, St. Michaels has a healthy tourism industry as guests come from far and near to enjoy all the wonderful things this charming community has to offer. There are upscale shops, historical sites and museums, seafood restaurants, boat tours, nearby golf courses, and so much more. Many will also recognize St. Michaels as the backdrop of several popular movies, including “The Wedding Crashers”! 

Would you like to experience this gorgeous, historical community for yourself? Eastern Shore Vacation Rentals has you covered! Simply scroll down to explore our variety of St Michaels, MD, vacation rentals, and reserve your favorite!

Browse Our St. Michaels Vacation Rentals Below

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Oyster Cottage

McDaniel
Beds: 4 | Baths: 4 | Sleeps: 8
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Acorn Point

Easton
Beds: 5 | Baths: 5.5 | Sleeps: 10
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PennyWhistle

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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Sunrise Cove

Saint Michaels
Beds: 4 | Baths: 3 | Sleeps: 8
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The Water House

St. Michaels
Beds: 5 | Baths: 5.5 | Sleeps: 9
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Town and Country

Saint Michaels
Beds: 4 | Baths: 3 | Sleeps: 8
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Carpenter Alley Cottage

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

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

Saint Michaels
Beds: 4 | Baths: 3 | Sleeps: 8
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Chesapeake Pines

Easton
Beds: 4 | Baths: 4 | Sleeps: 8
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Bushey Heath Farm

Royal Oak
Beds: 4 | Baths: 2 | Sleeps: 8
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Escape Farm

Royal Oak
Beds: 3 | Baths: 4 | Sleeps: 6
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Duck Cove

Neavitt
Beds: 2 | Baths: 1 | Sleeps: 4
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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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Emily's Lane

Wittman
Beds: 4 | Baths: 3.5 | Sleeps: 8
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At Tricefields Court

Saint Michaels
Beds: 4 | Baths: 5 | Sleeps: 8
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Heron Point

Royal Oak
Beds: 4 | Baths: 2.5 | Sleeps: 8
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Pines at Barrett Cove

Saint Michaels
Beds: 3 | Baths: 3 | Sleeps: 6
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Pines at Irish Creek

Royal Oak
Beds: 4 | Baths: 3 | Sleeps: 8
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Crabber's Cove

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

Saint Michaels
Beds: 5 | Baths: 4.5 | Sleeps: 10
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Caulk's Cove

Bozman
Beds: 3 | Baths: 2.5 | Sleeps: 6
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Mallard Point Cottage

McDaniel
Beds: 4 | Baths: 3 | Sleeps: 8
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Osprey Point

Saint Michaels
Beds: 4 | Baths: 3.5 | Sleeps: 8
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Special Offer! Riverview Retreat

Riverview Retreat

Saint Michaels
Beds: 3 | Baths: 2.5 | Sleeps: 6
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