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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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Chesapeake Bay Vacation Rentals in the Eastern Shore

Town and Country

Saint Michaels

Beds: 4 | Baths: 3 | Sleeps: 8

Willoughby

Cambridge

Beds: 7 | Baths: 6 | Sleeps: 24

The Landing

Saint Michaels

Beds: 4 | Baths: 3 | Sleeps: 8

PennyWhistle

McDaniel

Beds: 4 | Baths: 3 | Sleeps: 8

Escape Farm

Royal Oak

Beds: 3 | Baths: 4 | Sleeps: 6

Pride and Joy

Oxford

Beds: 3 | Baths: 2 | Sleeps: 6

McKendree Street Mainland

Annapolis

Beds: 4 | Baths: 3 | Sleeps: 8

22 Fleet Street

Annapolis

Beds: 3 | Baths: 2.5 | Sleeps: 6

Sunflower Cottage

Oxford

Beds: 2 | Baths: 1 | Sleeps: 4

The Water House

St. Michaels

Beds: 5 | Baths: 5.5 | Sleeps: 9

Holland Point Preserve

Taylors Island

Beds: 5 | Baths: 5 | Sleeps: 14

Mallard Point Cottage

McDaniel

Beds: 4 | Baths: 3 | Sleeps: 8

Clearview

Tilghman

Beds: 3 | Baths: 3 | Sleeps: 6

Sunrise Cove

Saint Michaels

Beds: 4 | Baths: 3 | Sleeps: 8

Captain's Cove

Saint Michaels

Beds: 5 | Baths: 4.5 | Sleeps: 10

Loblolly Cove

Neavitt

Beds: 4 | Baths: 3 | Sleeps: 8

Memory Lane

Oxford

Beds: 4 | Baths: 2full, 2 half | Sleeps: 8

Oxford Beach Cottage

Oxford

Beds: 3 | Baths: 2 | Sleeps: 6

Judith's Garden

Oxford

Beds: 4 | Baths: 2.5 | Sleeps: 8

Caulk's Cove

Bozman

Beds: 3 | Baths: 2.5 | Sleeps: 6

Indian Fields

Cambridge

Beds: 5 | Baths: 4.5 | Sleeps: 13

Carpenter Alley Cottage

St. Michaels

Beds: 3 | Baths: 3 | Sleeps: 6

Emily's Lane

Wittman

Beds: 4 | Baths: 3.5 | Sleeps: 8

Graceful View

Bozman

Beds: 3 | Baths: 2 | Sleeps: 6

Sycamore Acres

Easton

Beds: 6 | Baths: 5.5 | Sleeps: 12

East Street Easy Walk

Annapolis

Beds: 1 | Baths: 1.5 | Sleeps: 2