View All Properties

Feel free to browse our great selection of cottages, waterfront homes and estates. We would be happy to help you find just the right spot for your vacation! 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)

$756.00

Loblolly Cove
Bozman-Neavitt
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Loblolly Cove
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Starting at (USD)

$700.00

Lovely Cove Farm
Chestertown
  • 10 Guests
  • 4 Bedrooms
  • 2.5 Bathrooms
  • Code: Lovely Cove Farm
  • Pets Allowed
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Starting at (USD)

$420.00

Mallard Point Cottage
St. Michaels
  • 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
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Mallards Landing
  • Pets Allowed
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Starting at (USD)

$215.00

Martini Cottage
Oxford
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathrooms
  • Code: Martini Cottage
  • Pets Allowed
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Starting at (USD)

$315.00

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

$345.00

Middle Point Cottage
Bozman-Neavitt
  • 6 Guests
  • 3 Bedrooms
  • 1 Bathrooms
  • Code: Middle Point Cottage
  • Pets Allowed
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Starting at (USD)

$915.00

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

$567.00

Osprey Point
Royal Oak
  • 8 Guests
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Code: Osprey Point
  • Pets Allowed
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Starting at (USD)

$400.00

Oxbow Farm
Chestertown
  • 11 Guests
  • 5 Bedrooms
  • 4 Bathrooms
  • Code: Oxbow Farm
  • Pets Allowed
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Starting at (USD)

$371.00

Pandion
Bozman-Neavitt
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Pandion
  • Pets Allowed
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Starting at (USD)

$205.00

Parlour Suite on Morris
Oxford
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • Code: Parlour Suite on Morris
  • Pets Allowed
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Starting at (USD)

$570.00

PennyWhistle - St. Michaels MD
St. Michaels
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: PennyWhistle
  • Pets Allowed
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Starting at (USD)

$665.00

Pines at Barrett Cove
St. Michaels
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Pines at Barrett Cove
  • Pets Allowed
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Starting at (USD)

$570.00

Pines At Irish Creek
St. Michaels
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Pines at Irish Creek
  • Pets Allowed
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Starting at (USD)

$305.00

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

$313.00

Red Shake Cottage
Oxford
  • 8 Guests
  • 4 Bedrooms
  • 2 Bathrooms
  • Code: Red Shake Cottage
  • Pets Allowed
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Starting at (USD)

$327.00

Red White and View
St. Michaels
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Red White and View
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Starting at (USD)

$315.00

Seven Pines
Oxford
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • Code: Seven Pines
  • Pets Allowed
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Starting at (USD)

$305.00

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

$583.00

Sunrise Cove
Royal Oak
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Sunrise Cove
  • Pets Allowed
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Starting at (USD)

$525.00

Sunset Beach Cottage
Cambridge
  • 14 Guests
  • 7 Bedrooms
  • 4.5 Bathrooms
  • Code: Sunset Beach Cottage
  • Pets Allowed
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Starting at (USD)

$334.00

Sunset Retreat
Tilghman Island
  • 6 Guests
  • 3 Bedrooms
  • 1 Bathrooms
  • Code: Sunset Retreat
  • Pets Allowed
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Starting at (USD)

$590.00

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

$1,195.00

The Cove House
St. Michaels
  • 12 Guests
  • 5 Bedrooms
  • 5 Bathrooms
  • Code: The Cove House
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