Homes with Pools

Homes with Pools

There’s nothing like sipping on sweet tea as you sunbathe at your own private pool. Did you immediately imagine yourself enjoying this relaxing experience? Well, luckily for you, it doesn’t have to remain a daydream. Our collection of properties includes a wide variety of Eastern Shore, MD, vacation rentals with pools. Don’t worry about driving, trying to obtain a pass, or dealing with the crowds at public pools during your next vacation. Simply step outside and dip your toes into the cool, soothing waters of your own pool!

You’re only a few clicks away from finding your ideal vacation rental in the St. Michaels area. Put the pause on simply picturing this dreamy scene and start planning it! Scroll down and explore our vacation rentals with private pools on Maryland’s Eastern Shore. You won’t regret it!

View Our Eastern Shore, MD, Vacation Rentals With Pools

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Sunrise Cove

Saint Michaels
Beds: 4 | Baths: 3 | Sleeps: 8
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Belle Aire Landing

East New Market
Beds: 9 | Baths: 6 | Sleeps: 22
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Nantucket on the Chesapeake

Annapolis
Beds: 4 | Baths: 3.5 | Sleeps: 10
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Creek Cottage

Centreville
Beds: 4 | Baths: 4 | Sleeps: 10
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Sycamore Acres

Easton
Beds: 6 | Baths: 5.5 | Sleeps: 12
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Acorn Point

Easton
Beds: 5 | Baths: 5.5 | Sleeps: 10
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Blue Gates

Easton
Beds: 4 | Baths: 4 | Sleeps: 10
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Thornton

Chestertown
Beds: 6 | Baths: 4.5 | Sleeps: 11
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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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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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Hudson Manor

Cambridge
Beds: 7 | Baths: 6 | Sleeps: 22
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Mill Creek

Wye Mills
Beds: 5 | Baths: 3.5 | Sleeps: 10
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Pines at Barrett Cove

Saint Michaels
Beds: 3 | Baths: 3 | Sleeps: 6
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At Tricefields Court

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

Saint Michaels
Beds: 4 | Baths: 3.5 | Sleeps: 8
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Town and Country

Saint Michaels
Beds: 4 | Baths: 3 | Sleeps: 10
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Clearview

Tilghman
Beds: 3 | Baths: 3 | Sleeps: 6
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Heron Point

Royal Oak
Beds: 4 | Baths: 2.5 | Sleeps: 8
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Retreat on Grace Creek

Bozman
Beds: 6 | Baths: 8 | Sleeps: 12
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Fairview

Easton
Beds: 5 | Baths: 6 | Sleeps: 10
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Indian Fields

Cambridge
Beds: 5 | Baths: 4.5 | Sleeps: 13
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Oxford Oasis

Oxford
Beds: 6 | Baths: 7 | Sleeps: 12
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Escape Farm

Royal Oak
Beds: 3 | Baths: 4 | Sleeps: 6
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Swan's Rest

Easton
Beds: 3 | Baths: 3 | Sleeps: 6
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Lee Haven

Easton
Beds: 5 | Baths: 4.5 | Sleeps: 10
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Loblolly Cove

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

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

Cambridge
Beds: 7 | Baths: 5.5 | Sleeps: 17
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Broadwater View

Royal Oak
Beds: 5 | Baths: 4.5 | Sleeps: 10
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Emily's Lane

Wittman
Beds: 4 | Baths: 3.5 | Sleeps: 8
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Cedar Cove on the Miles

Easton
Beds: 4 | Baths: 4 | Sleeps: 8
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Gladimere

Easton
Beds: 3 | Baths: 3 | Sleeps: 6
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