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. They 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 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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Blue Gates FROM $6370

Blue Gates

Beds: 4 | Baths: 4 | Sleeps: 10
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Acorn Point FROM $8500

Acorn Point

Beds: 5 | Baths: 5.5 | Sleeps: 10
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Retreat on Grace Creek FROM $11000

Retreat on Grace Creek

Beds: 6 | Baths: 8 | Sleeps: 12
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