An Eastern Shore, MD, cottage rental

Cottages

What does your happy place look like? If it’s a cozy cottage surrounded by natural scenery, then you’re on the right page — and on your way toward that happy place you’re picturing! We have several Eastern Shore, MD, cottage rentals for you to choose from, featuring comfortable accommodations and gorgeous views in peaceful settings. These are the ideal properties for clearing your mind and reconnecting with nature as you discover the true meaning of relaxation. 

Are you ready to take the next step toward an unbelievable vacation? Browse our cottage rentals on the Eastern Shore of Maryland below. You’re sure to find your ideal destination!

Peruse Our Eastern Shore, MD, Cottage Rentals


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Broadwater View

Royal Oak
Beds: 5 | Baths: 4.5 | Sleeps: 10
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The Water House

St. Michaels
Beds: 5 | Baths: 6 | Sleeps: 9
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Windward Cove

Grasonville
Beds: 4 | Baths: 3 | Sleeps: 8
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Indian Fields

Cambridge
Beds: 5 | Baths: 4.5 | Sleeps: 13
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Serenity in St. Michaels

Saint Michaels
Beds: 5 | Baths: 4.5 | Sleeps: 4
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East Street Easy Walk

Annapolis
Beds: 1 | Baths: 1.5 | Sleeps: 2
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Hudson Manor

Cambridge
Beds: 7 | Baths: 6 | Sleeps: 22
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McKendree Street Mainland

Annapolis
Beds: 4 | Baths: 3 | Sleeps: 8
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Bay Water Cottage

Church Creek
Beds: 4 | Baths: 3.5 | Sleeps: 8
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Creek Cottage

Centreville
Beds: 4 | Baths: 4 | Sleeps: 10
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Pines at Barrett Cove

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

Cambridge
Beds: 4 | Baths: 3.5 | Sleeps: 10
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Sunrise Cove

Saint Michaels
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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Judith's Garden

Oxford
Beds: 4 | Baths: 2.5 | Sleeps: 8
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The Bay House on Easy Lane

Centreville
Beds: 3 | Baths: 3.5 | Sleeps: 8
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Thornton

Chestertown
Beds: 6 | Baths: 4.5 | Sleeps: 11
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Mallard Point Cottage

McDaniel
Beds: 4 | Baths: 3 | Sleeps: 8
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Duck Cove

Neavitt
Beds: 2 | Baths: 1 | Sleeps: 4
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The Bird's Nest

Cambridge
Beds: 5 | Baths: 3.5 | Sleeps: 16
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At Tricefields Court

Saint Michaels
Beds: 4 | Baths: 5 | Sleeps: 8
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Pride and Joy

Oxford
Beds: 3 | Baths: 2 | Sleeps: 6
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Waverly

Easton
Beds: 5 | Baths: 5.5 | Sleeps: 10
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Riverview Retreat

Saint Michaels
Beds: 3 | Baths: 2.5 | Sleeps: 6
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Cedar Cove on the Miles

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

Oxford
Beds: 2 | Baths: 1 | Sleeps: 4
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Carpenter Alley Cottage

St. Michaels
Beds: 3 | Baths: 3 | Sleeps: 6
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The Landing

Saint Michaels
Beds: 4 | Baths: 3 | Sleeps: 8
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Mill Creek

Wye Mills
Beds: 5 | Baths: 3.5 | Sleeps: 10
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Nantucket on the Chesapeake

Annapolis
Beds: 4 | Baths: 2.5 | Sleeps: 8
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Memory Lane

Oxford
Beds: 4 | Baths: 2full, 2 half | Sleeps: 8
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Willoughby

Cambridge
Beds: 7 | Baths: 6 | Sleeps: 24
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Ben Oaks Drive

Severna Park
Beds: 4 | Baths: 2.5 | Sleeps: 10
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Crabber's Cove

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

Cambridge
Beds: 7 | Baths: 5.5 | Sleeps: 18
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Oxford Beach Cottage

Oxford
Beds: 3 | Baths: 2 | Sleeps: 6
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Tidal Serenity

Taylors Island
Beds: 5 | Baths: 2.5 | Sleeps: 15
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Clearview

Tilghman
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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Simplicity Cottage

Tilghman
Beds: 2 | Baths: 1.5 | Sleeps: 4
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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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Chesapeake Pines

Easton
Beds: 4 | Baths: 4 | Sleeps: 8
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22 Fleet Street

Annapolis
Beds: 3 | Baths: 2.5 | Sleeps: 6
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Escape Farm

Royal Oak
Beds: 3 | Baths: 4 | Sleeps: 6
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Captain's Cove

Saint Michaels
Beds: 5 | Baths: 4.5 | Sleeps: 10
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Bushey Heath Farm

Royal Oak
Beds: 4 | Baths: 2 | Sleeps: 8
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Graceful View

Bozman
Beds: 3 | Baths: 2 | Sleeps: 6
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Retreat on Grace Creek

Bozman
Beds: 6 | Baths: 8 | Sleeps: 12
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Oxford Oasis

Oxford
Beds: 6 | Baths: 7 | Sleeps: 12
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Acorn Point

Easton
Beds: 5 | Baths: 5.5 | Sleeps: 10
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Belle Aire Landing

East New Market
Beds: 9 | Baths: 6 | Sleeps: 22
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Blue Gates

Easton
Beds: 4 | Baths: 4 | Sleeps: 8
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Town and Country

Saint Michaels
Beds: 4 | Baths: 3 | Sleeps: 8
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Loblolly Cove

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