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Check out the category groups below to find your next Eastern Shore vacation rental in Maryland! Located in and around the St Michaels area, our vacation rentals offer great opportunities for exploring, adventure and relaxing. Enjoy breathtaking scenic views of the ocean and bay, hot tubs, fire pits, and beautifully cared for properties.

Guests often take advantage of nearby fishing and crabbing holes as well as the area beaches and attractions. Whether you are looking to get outdoors, see the nearby towns, or spend the days on the sand, we offer a wide variety of rentals with great amenities and features.

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)

$430.00

Mallard Point Cottage
McDaniel, MD
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Mallard Point Cottage
  • Pets Allowed
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Starting at (USD)

$620.00

Mallard's Landing
Easton, MD
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Mallards Landing
  • Pets Allowed
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Starting at (USD)

$305.00

Memory Lane
Oxford, MD
  • 8 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • Code: Memory Lane
  • Pets Allowed
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Starting at (USD)

$915.00

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

$590.00

Osprey Point
Saint Michaels, MD
  • 8 Guests
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Code: Osprey Point
  • Pets Allowed
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Starting at (USD)

$360.00

Oxford Beach Cottage
Oxford, MD
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Oxford Beach Cottage
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Starting at (USD)

$650.00

Oxford Oasis
Oxford, MD
  • 12 Guests
  • 6 Bedrooms
  • 7 Bathrooms
  • Code: Oxford Oasis
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Starting at (USD)

$540.00

PennyWhistle
McDaniel, MD
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: PennyWhistle
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Starting at (USD)

$740.00

Pines at Barrett Cove
Saint Michaels, MD
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Pines at Barrett Cove
  • Pets Allowed
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Starting at (USD)

$530.00

Pines At Irish Creek
Royal Oak, MD
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Pines at Irish Creek
  • Pets Allowed
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Starting at (USD)

$335.00

Pride and Joy
Oxford, MD
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Pride and Joy Cottage
  • Pets Allowed
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Starting at (USD)

$350.00

Queen Anne
Easton, MD
  • 8 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • Code: Queen Anne
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Starting at (USD)

$350.00

Red Shake Cottage
Oxford, MD
  • 8 Guests
  • 4 Bedrooms
  • 2 Bathrooms
  • Code: Red Shake Cottage
  • Pets Allowed
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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)

$335.00

Simplicity Cottage
Tilghman Island, MD
  • 4 Guests
  • 2 Bedrooms
  • 1.5 Bathrooms
  • Code: Simplicity Cottage
  • Pets Allowed
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Starting at (USD)

$585.00

Sunrise Cove
Saint Michaels, MD
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Sunrise Cove
  • Pets Allowed
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Starting at (USD)

$595.00

Swan's Rest
Easton, MD
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Swans Rest
  • Pets Allowed
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Starting at (USD)

$645.00

Thistle Dew
Easton, MD
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Thistle Dew
  • Pets Allowed
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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)

$550.00

Town Creek Haven
Oxford, MD
  • 8 Guests
  • 3 Bedrooms
  • 3.5 Bathrooms
  • Code: Town Creek Haven
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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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