Luxury Homes

Looking for more than just the comforts of home? Our luxury vacation home rentals offer extra amenities not found in your typical rental. Upscale furnishings and luxury touches such as a private swimming pool, dock, multiple acres, high-end kitchens or amazing outdoor spaces are found in many of our luxury rental homes on Marylands Eastern Shore. Feel free to browse these fantastic properties and make your vacation to the Eastern Shore one to remember!

Please note prices below per night, based on the summer weekly price for seven nights and are given as a range to assist you with choosing a property. Nightly prices vary per season and per number of nights booked. For an exact quote, please input your dates on the property page.

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Starting at (USD)

$1,287.00

Acorn Point
Easton, MD
  • 10 Guests
  • 5 Bedrooms
  • 5.5 Bathrooms
  • Code: Acorn Point
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Starting at (USD)

$1,150.00

Bayberry Cove
Cambridge, MD
  • 17 Guests
  • 7 Bedrooms
  • 5.5 Bathrooms
  • Code: Bayberry Cove
  • Pets Allowed
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Starting at (USD)

$1,050.00

Blue Gates
Easton, MD
  • 10 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • Code: Blue Gates
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Starting at (USD)

$970.00

Broadwater View
Royal Oak, MD
  • 10 Guests
  • 5 Bedrooms
  • 4.5 Bathrooms
  • Code: Broadwater View
  • Pets Allowed
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Starting at (USD)

$930.00

Captain's Cove
Saint Michaels, MD
  • 10 Guests
  • 5 Bedrooms
  • 4.5 Bathrooms
  • Code: Captain`s Cove
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Starting at (USD)

$1,300.00

Hudson Manor
Cambridge, MD
  • 22 Guests
  • 7 Bedrooms
  • 6 Bathrooms
  • Code: Hudson Manor
  • Pets Allowed
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Starting at (USD)

$975.00

Off the Grid
Oxford, MD
  • 10 Guests
  • 5 Bedrooms
  • 4.5 Bathrooms
  • Code: Off the Grid
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Starting at (USD)

$1,237.00

Retreat on Grace Creek
Bozman, MD
  • 12 Guests
  • 6 Bedrooms
  • 8 Bathrooms
  • Code: Retreat on Grace Creek
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Starting at (USD)

$1,045.00

Thornton Farm - Grace and Elegance
Chestertown, MD
  • 11 Guests
  • 6 Bedrooms
  • 4.5 Bathrooms
  • Code: Thornton
  • Pets Allowed
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Starting at (USD)

$880.00

Town & Country
Saint Michaels, MD
  • 10 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Town & Country
  • Pets Allowed
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Starting at (USD)

$820.00

Tricefields - A Tidewater Colonial
Saint Michaels, MD
  • 8 Guests
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Code: Tricefields
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Easton, MD
  • 10 Guests
  • 5 Bedrooms
  • 5.5 Bathrooms
  • Code: Waverly
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Starting at (USD)

$1,215.00

Willoughby
Cambridge, MD
  • 24 Guests
  • 7 Bedrooms
  • 6 Bathrooms
  • Code: Willoughby
  • Pets Allowed
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Starting at (USD)

$1,225.00

Woodwind
Easton, MD
  • 10 Guests
  • 5 Bedrooms
  • 4 Bathrooms
  • Code: Woodwind
  • Pets Allowed
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