The bathroom inside a luxury vacation rental on the Eastern Shore of MD

Luxury Properties

You might wish that you could escape the stresses of daily life and enjoy a relaxing vacation whenever — and as often — as you’d like. However, that’s just not always a realistic option. So, why not make the most out of the vacations you do get to take each year? Our luxury vacation rentals on the Eastern Shore of MD provide the perfect settings to help make that happen. Our luxury vacation rentals in Maryland come with the utmost comforts and amenities to ensure that stress is the furthest thing from your mind as you settle into your property each day. 

Whether you’re looking for luxury Maryland vacation rentals in St. Michaels, Chestertown, Oxford, or beyond, we have the ideal property waiting for you. So, what are you waiting for? It’s time to treat yourself to the luxurious getaway that you deserve. Explore our gorgeous vacation homes on the Eastern Shore now and find your happy place!

Browse Our Luxury Vacation Rentals on the Eastern Shore of MD

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At Tricefields Court

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

Chestertown
Beds: 6 | Baths: 4.5 | Sleeps: 11
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Acorn Point

Easton
Beds: 5 | Baths: 5.5 | Sleeps: 10
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Broadwater View

Royal Oak
Beds: 5 | Baths: 4.5 | Sleeps: 10
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Captain's Cove

Saint Michaels
Beds: 5 | Baths: 4.5 | Sleeps: 10
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Retreat on Grace Creek

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

Cambridge
Beds: 7 | Baths: 6 | Sleeps: 24
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Bayberry Cove

Cambridge
Beds: 7 | Baths: 5.5 | Sleeps: 18
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Town and Country

Saint Michaels
Beds: 4 | Baths: 3 | Sleeps: 8
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Blue Gates

Easton
Beds: 4 | Baths: 4 | 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: 2.5 | Sleeps: 8
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Hudson Manor

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