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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Special Offer! Pines at Irish Creek FROM $2720

Pines at Irish Creek

Royal Oak
Beds: 4 | Baths: 3 | Sleeps: 8
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Special Offer! Emily's Lane FROM $4500

Emily's Lane

Wittman
Beds: 4 | Baths: 3.5 | Sleeps: 8
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Special Offer! The Landing FROM $4000

The Landing

Saint Michaels
Beds: 4 | Baths: 3 | Sleeps: 8
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PennyWhistle FROM $2750

PennyWhistle

McDaniel
Beds: 4 | Baths: 3 | Sleeps: 8
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Special Offer! The Water House FROM $3500 - $4200

The Water House

St. Michaels
Beds: 5 | Baths: 5.5 | Sleeps: 9
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Special Offer! Town and Country FROM $4900

Town and Country

Saint Michaels
Beds: 4 | Baths: 3 | 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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Special Offer! Graceful View FROM $2450

Graceful View

Bozman
Beds: 3 | Baths: 2 | Sleeps: 6
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Special Offer! Carpenter Alley Cottage FROM $1750

Carpenter Alley Cottage

St. Michaels
Beds: 3 | Baths: 3 | Sleeps: 6
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Duck Cove FROM $1200

Duck Cove

Neavitt
Beds: 2 | Baths: 1 | Sleeps: 4
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Special Offer! Mallard Point Cottage FROM $2050

Mallard Point Cottage

McDaniel
Beds: 4 | Baths: 3 | Sleeps: 8
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Special Offer! Caulk's Cove FROM $1890

Caulk's Cove

Bozman
Beds: 3 | Baths: 2.5 | Sleeps: 6
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Special Offer! Broadwater View FROM $5800

Broadwater View

Royal Oak
Beds: 5 | Baths: 4.5 | Sleeps: 10
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Special Offer! Escape Farm FROM $3000

Escape Farm

Royal Oak
Beds: 3 | Baths: 4 | Sleeps: 6
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Special Offer! Bushey Heath Farm FROM $3500

Bushey Heath Farm

Royal Oak
Beds: 4 | Baths: 2 | Sleeps: 8
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Acorn Point FROM $8500

Acorn Point

Easton
Beds: 5 | Baths: 5.5 | Sleeps: 10
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Special Offer! Crabber's Cove FROM $2400 - $2750

Crabber's Cove

St. Michaels
Beds: 3 | Baths: 3 | Sleeps: 6
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Special Offer! Osprey Point FROM $3225

Osprey Point

Saint Michaels
Beds: 4 | Baths: 3.5 | Sleeps: 8
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Special Offer! Loblolly Cove FROM $4075

Loblolly Cove

Neavitt
Beds: 4 | Baths: 3 | Sleeps: 8
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Special Offer! Heron Point FROM $4250

Heron Point

Royal Oak
Beds: 4 | Baths: 2.5 | Sleeps: 8
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Special Offer! Captain's Cove FROM $5625

Captain's Cove

Saint Michaels
Beds: 5 | Baths: 4.5 | Sleeps: 10
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Special Offer! Pines at Barrett Cove FROM $4025

Pines at Barrett Cove

Saint Michaels
Beds: 3 | Baths: 3 | Sleeps: 6
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Special Offer! Sunrise Cove FROM $3000

Sunrise Cove

Saint Michaels
Beds: 4 | Baths: 3 | Sleeps: 8
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Special Offer! Chesapeake Pines FROM $2100

Chesapeake Pines

Easton
Beds: 4 | Baths: 4 | Sleeps: 8
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Special Offer! At Tricefields Court FROM $4500

At Tricefields Court

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