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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Thornton FROM $4500 - $6000

Thornton

Chestertown
Beds: 6 | Baths: 4.5 | Sleeps: 11
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Ben Oaks Drive FROM $5800

Ben Oaks Drive

Severna Park
Beds: 4 | Baths: 2.5 | Sleeps: 10
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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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Lee Haven FROM $5250

Lee Haven

Easton
Beds: 5 | Baths: 4.5 | Sleeps: 10
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Chesapeake Pines FROM $2100

Chesapeake Pines

Easton
Beds: 4 | Baths: 4 | Sleeps: 8
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Belle Aire Landing FROM $11900

Belle Aire Landing

East New Market
Beds: 9 | Baths: 6 | Sleeps: 22
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Clearview FROM $2850

Clearview

Tilghman
Beds: 3 | Baths: 3 | Sleeps: 6
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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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Creek Cottage FROM $4750

Creek Cottage

Centreville
Beds: 4 | Baths: 4 | Sleeps: 10
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Tidal Serenity FROM $2850

Tidal Serenity

Taylors Island
Beds: 5 | Baths: 2.5 | Sleeps: 15
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Bayberry Cove FROM $7000

Bayberry Cove

Cambridge
Beds: 7 | Baths: 5.5 | Sleeps: 17
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Heron Point FROM $4250

Heron Point

Royal Oak
Beds: 4 | Baths: 2.5 | 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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Retreat on Grace Creek FROM $11000

Retreat on Grace Creek

Bozman
Beds: 6 | Baths: 8 | Sleeps: 12
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Memory Lane FROM $1250

Memory Lane

Oxford
Beds: 4 | Baths: 2full, 2 half | Sleeps: 8
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McKendree Street Mainland FROM $2889 - $8500

McKendree Street Mainland

Annapolis
Beds: 4 | Baths: 3 | Sleeps: 10
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Town and Country FROM $4900

Town and Country

Saint Michaels
Beds: 4 | Baths: 3 | Sleeps: 10
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At Tricefields Court FROM $4500

At Tricefields Court

Saint Michaels
Beds: 4 | Baths: 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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Pines at Irish Creek FROM $2720

Pines at Irish Creek

Royal Oak
Beds: 4 | Baths: 3 | Sleeps: 8
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Holland Point Preserve FROM $4165

Holland Point Preserve

Taylors Island
Beds: 5 | Baths: 5 | Sleeps: 14
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Pride and Joy FROM $1500

Pride and Joy

Oxford
Beds: 3 | Baths: 2 | Sleeps: 6
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Escape Farm FROM $3000

Escape Farm

Royal Oak
Beds: 3 | Baths: 4 | Sleeps: 6
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Simplicity Cottage FROM $1500

Simplicity Cottage

Tilghman
Beds: 2 | Baths: 1.5 | Sleeps: 4
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Cedar Cove on the Miles FROM $3450

Cedar Cove on the Miles

Easton
Beds: 4 | Baths: 4 | Sleeps: 8
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Oxford Beach Cottage FROM $1850

Oxford Beach Cottage

Oxford
Beds: 3 | Baths: 2 | Sleeps: 6
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Blue Gates FROM $6370

Blue Gates

Easton
Beds: 4 | Baths: 4 | Sleeps: 10
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The Landing FROM $4000

The Landing

Saint Michaels
Beds: 4 | Baths: 3 | Sleeps: 8
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Willoughby FROM $5250 - $7750

Willoughby

Cambridge
Beds: 7 | Baths: 6 | Sleeps: 24
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Indian Fields FROM $3500

Indian Fields

Cambridge
Beds: 5 | Baths: 4.5 | Sleeps: 13
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Acorn Point FROM $8500

Acorn Point

Easton
Beds: 5 | Baths: 5.5 | Sleeps: 10
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Sycamore Acres FROM $5850

Sycamore Acres

Easton
Beds: 6 | Baths: 5.5 | Sleeps: 12
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Bay Water Cottage FROM $2135

Bay Water Cottage

Church Creek
Beds: 4 | Baths: 3.5 | 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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Nantucket on the Chesapeake FROM $3940 - $10500

Nantucket on the Chesapeake

Annapolis
Beds: 4 | Baths: 3.5 | Sleeps: 10
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Mallard Point Cottage FROM $2050

Mallard Point Cottage

McDaniel
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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Sunflower Cottage FROM $1250

Sunflower Cottage

Oxford
Beds: 2 | Baths: 1 | Sleeps: 4
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Mill Creek FROM $4750

Mill Creek

Wye Mills
Beds: 5 | Baths: 3.5 | Sleeps: 10
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Fairview FROM $12500

Fairview

Easton
Beds: 5 | Baths: 6 | Sleeps: 10
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Oxford Oasis FROM $4900

Oxford Oasis

Oxford
Beds: 6 | Baths: 7 | Sleeps: 12
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Broadwater View FROM $5800

Broadwater View

Royal Oak
Beds: 5 | Baths: 4.5 | Sleeps: 10
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The Bay House on Easy Lane FROM $3800

The Bay House on Easy Lane

Centreville
Beds: 3 | Baths: 3.5 | Sleeps: 8
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Duck Cove FROM $1200

Duck Cove

Neavitt
Beds: 2 | Baths: 1 | Sleeps: 4
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Emily's Lane FROM $4500

Emily's Lane

Wittman
Beds: 4 | Baths: 3.5 | Sleeps: 10
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22 Fleet Street FROM $2793 - $14000

22 Fleet Street

Annapolis
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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Loblolly Cove FROM $4075

Loblolly Cove

Neavitt
Beds: 4 | Baths: 3 | Sleeps: 8
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Swan's Rest FROM $3050

Swan's Rest

Easton
Beds: 3 | Baths: 3 | Sleeps: 6
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Graceful View FROM $2450

Graceful View

Bozman
Beds: 3 | Baths: 2 | Sleeps: 6
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Judith's Garden FROM $4600

Judith's Garden

Oxford
Beds: 4 | Baths: 2.5 | Sleeps: 8
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Hudson Manor FROM $6500

Hudson Manor

Cambridge
Beds: 7 | Baths: 6 | Sleeps: 22
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Waverly

Easton
Beds: 5 | Baths: 5.5 | Sleeps: 10
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Bushey Heath Farm FROM $3500

Bushey Heath Farm

Royal Oak
Beds: 4 | Baths: 2 | 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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