An Eastern Shore, MD, vacation rental with a pool

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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Judith's Garden FROM $4600

Judith's Garden

Oxford
Beds: 4 | Baths: 2.5 | Sleeps: 8
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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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Cedar Cove on the Miles FROM $3450

Cedar Cove on the Miles

Easton
Beds: 4 | Baths: 4 | Sleeps: 8
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Heron Point FROM $4250

Heron Point

Royal Oak
Beds: 4 | Baths: 2.5 | Sleeps: 8
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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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Loblolly Cove FROM $4075

Loblolly Cove

Neavitt
Beds: 4 | Baths: 3 | Sleeps: 8
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Sycamore Acres FROM $5850

Sycamore Acres

Easton
Beds: 6 | Baths: 5.5 | Sleeps: 12
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Sunrise Cove FROM $3000

Sunrise Cove

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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Indian Fields FROM $3500

Indian Fields

Cambridge
Beds: 5 | Baths: 4.5 | Sleeps: 13
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Swan's Rest FROM $3050

Swan's Rest

Easton
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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Bushey Heath Farm FROM $3500

Bushey Heath Farm

Royal Oak
Beds: 4 | Baths: 2 | Sleeps: 8
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Hudson Manor FROM $6500

Hudson Manor

Cambridge
Beds: 7 | Baths: 6 | Sleeps: 22
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Thornton FROM $4500 - $6000

Thornton

Chestertown
Beds: 6 | Baths: 4.5 | Sleeps: 11
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Emily's Lane FROM $4500

Emily's Lane

Wittman
Beds: 4 | Baths: 3.5 | 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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Mill Creek FROM $4750

Mill Creek

Wye Mills
Beds: 5 | Baths: 3.5 | Sleeps: 10
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Creek Cottage FROM $4750

Creek Cottage

Centreville
Beds: 4 | Baths: 4 | 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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Waverly

Easton
Beds: 5 | Baths: 5.5 | Sleeps: 10
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Clearview FROM $2850

Clearview

Tilghman
Beds: 3 | Baths: 3 | 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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At Tricefields Court FROM $4500

At Tricefields Court

Saint Michaels
Beds: 4 | Baths: 5 | Sleeps: 8
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Bayberry Cove FROM $7000

Bayberry Cove

Cambridge
Beds: 7 | Baths: 5.5 | Sleeps: 17
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Blue Gates FROM $6370

Blue Gates

Easton
Beds: 4 | Baths: 4 | Sleeps: 10
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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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Escape Farm FROM $3000

Escape Farm

Royal Oak
Beds: 3 | Baths: 4 | Sleeps: 6
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Acorn Point FROM $8500

Acorn Point

Easton
Beds: 5 | Baths: 5.5 | Sleeps: 10
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Lee Haven FROM $5250

Lee Haven

Easton
Beds: 5 | Baths: 4.5 | 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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Osprey Point FROM $3225

Osprey Point

Saint Michaels
Beds: 4 | Baths: 3.5 | Sleeps: 8
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Broadwater View FROM $5800

Broadwater View

Royal Oak
Beds: 5 | Baths: 4.5 | Sleeps: 10
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