Memorial Day Weekend

Join us for the unofficial start to summer! Kick off the warm weather with a waterfront home and Chesapeake Bay breezes!

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Starting at (USD)

$360.00

Bay Water Cottage
Cambridge
  • 8 Guests
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Code: Bay Water Cottage
View Rental
Starting at (USD)

$427.00

Bird Dog Run
St. Michaels
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Bird Dog Run
  • Pets Allowed
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Starting at (USD)

$557.00

Bushey Heath Farm
Royal Oak
  • 8 Guests
  • 4 Bedrooms
  • 2 Bathrooms
  • Code: Bushey Heath Farm
  • Pets Allowed
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Starting at (USD)

$529.00

Captain`s Cottage
Easton
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Captains Cottage
  • Pets Allowed
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Starting at (USD)

$323.00

Caulk`s Cove
Bozman-Neavitt
  • 8 Guests
  • 3 Bedrooms
  • 2.5 Bathrooms
  • Code: Caulks Cove
  • Pets Allowed
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Starting at (USD)

$509.00

Clearview
Tilghman Island
  • 7 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Clearview
  • Pets Allowed
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Starting at (USD)

$855.00

Creek Cottage
Centreville
  • 10 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • Code: Creek Cottage
  • Pets Allowed
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Starting at (USD)

$1,125.00

Crosswinds
Tilghman Island
  • 12 Guests
  • 6 Bedrooms
  • 5.5 Bathrooms
  • Code: Crosswinds
  • Pets Allowed
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Starting at (USD)

$185.00

Dukes Street Cottage
Easton
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • Code: Dukes Street Cottage
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Starting at (USD)

$580.00

Gladimere
Easton
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Gladimere Glad I`m Here
  • Pets Allowed
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Starting at (USD)

$575.00

Grace Creek Cottage
Bozman-Neavitt
  • 6 Guests
  • 3 Bedrooms
  • 1.5 Bathrooms
  • Code: Grace Creek Cottage
  • Pets Allowed
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Starting at (USD)

$285.00

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

$760.00

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

$1,300.00

Hudson Manor
Cambridge
  • 22 Guests
  • 7 Bedrooms
  • 6 Bathrooms
  • Code: Hudson Manor
  • Pets Allowed
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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)

$430.00

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

$215.00

Martini Cottage
Oxford
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathrooms
  • Code: Martini Cottage
  • Pets Allowed
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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

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)

$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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