Chesapeake Bay Vacation Rentals in the Eastern Shore

We offer a wide variety of Eastern Shore vacation rentals in Maryland from St Michaels to Oxford and everywhere in between. Below you will find different Chesapeake Bay vacation rentals by category based on location or your desired amenities. You can choose vacation rentals that are great for large groups, rentals that have a pool and pet-friendly rentals. We truly have something for everyone as you book your Chesapeake Bay vacation! Start exploring today. We can't wait to help you find the perfect Maryland vacation rental.

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Starting at (USD)

$800.00

At Tricefields Court
Saint Michaels, MD
  • 8 Guests
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Code: At Tricefields Court
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Starting at (USD)

$425.00

Back Street Cottage
Easton, MD
  • 6 Guests
  • 3 Bedrooms
  • 1.5 Bathrooms
  • Code: Back Street Cottage
  • Pets Allowed
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Starting at (USD)

$400.00

Bay Water Cottage
Church Creek, MD
  • 8 Guests
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Code: Bay Water Cottage
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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)

$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)

$525.00

Bushey Heath Farm
Royal Oak, MD
  • 8 Guests
  • 4 Bedrooms
  • 2 Bathrooms
  • Code: Bushey Heath Farm
  • 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)

$335.00

Carpenter Alley Cottage
Saint Michaels, MD
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Carpenter Alley
  • Pets Allowed
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Starting at (USD)

$355.00

Caulk's Cove
Bozman, MD
  • 6 Guests
  • 3 Bedrooms
  • 2.5 Bathrooms
  • Code: Caulks Cove
  • Pets Allowed
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Starting at (USD)

$605.00

Cedar Cove on the Miles
Easton, MD
  • 8 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • Code: Cedar Cove on the Miles
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Starting at (USD)

$415.00

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

$505.00

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

$425.00

Crabber's Cove
Saint Michaels, MD
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Crabbers Cove
  • Pets Allowed
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Starting at (USD)

$815.00

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

$730.00

Emily's Lane
Wittman, MD
  • 8 Guests
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Code: Emily`s Lane
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Starting at (USD)

$535.00

Escape Farm
Royal Oak, MD
  • 6 Guests
  • 3 Bedrooms
  • 4 Bathrooms
  • Code: Escape Farm
  • Pets Allowed
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Starting at (USD)

$899.00

Fleet Street
Annapolis, MD
  • 6 Guests
  • 3 Bedrooms
  • 2.5 Bathrooms
  • Code: Fleet Street
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Starting at (USD)

$530.00

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

$295.00

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

$720.00

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

$665.00

Holland Point Preserve
Taylors Island, MD
  • 14 Guests
  • 5 Bedrooms
  • 5 Bathrooms
  • Code: Holland Point Preserve
  • Pets Allowed
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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)

$630.00

Indian Fields
Cambridge, MD
  • 13 Guests
  • 5 Bedrooms
  • 4.5 Bathrooms
  • Code: Indian Fields
  • Pets Allowed
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Starting at (USD)

$715.00

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

$395.00

Mallard Point Cottage
McDaniel, MD
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Mallard Point Cottage
  • Pets Allowed
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