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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

Judith's Garden

Oxford

Beds: 4 | Baths: 2.5 | Sleeps: 8

Mallard Point Cottage

McDaniel

Beds: 4 | Baths: 3 | Sleeps: 8

Sunrise Cove

Saint Michaels

Beds: 4 | Baths: 3 | Sleeps: 8

Osprey Point

Saint Michaels

Beds: 4 | Baths: 3.5 | Sleeps: 8

Retreat on Grace Creek

Bozman

Beds: 6 | Baths: 8 | Sleeps: 12

The Cabin at Broad Creek

Bozman

Beds: 5 | Baths: 3 | Sleeps: 10

Oxford Beach Cottage

Oxford

Beds: 3 | Baths: 2 | Sleeps: 6

Nantucket on the Chesapeake

Annapolis

Beds: 4 | Baths: 2.5 | Sleeps: 8

Heron Point

Royal Oak

Beds: 4 | Baths: 2.5 | Sleeps: 8

Ben Oaks Drive

Severna Park

Beds: 4 | Baths: 2.5 | Sleeps: 10

Thornton

Chestertown

Beds: 6 | Baths: 4.5 | Sleeps: 13

Thorntonwood

Bozman

Beds: 4 | Baths: 2.5 | Sleeps: 8

Pride and Joy

Oxford

Beds: 3 | Baths: 2 | Sleeps: 6

Flo Farm

Cambridge

Beds: 7 | Baths: 6.5 | Sleeps: 16

Hudson Manor

Cambridge

Beds: 7 | Baths: 6 | Sleeps: 22

Blue Gates

Easton

Beds: 4 | Baths: 4 | Sleeps: 8

Leeds Landing

Easton

Beds: 4 | Baths: 3 | Sleeps: 8

Bayberry Cove

Cambridge

Beds: 7 | Baths: 5.5 | Sleeps: 18

22 Fleet Street

Annapolis

Beds: 3 | Baths: 2.5 | Sleeps: 6

Crabber's Cove

St. Michaels

Beds: 3 | Baths: 3 | Sleeps: 6

Emily's Lane

Wittman

Beds: 4 | Baths: 3.5 | Sleeps: 8

Creek Cottage at Reed Creek Farm

Centreville

Beds: 4 | Baths: 4 | Sleeps: 10

Cedar Cove on the Miles

Easton

Beds: 4 | Baths: 4 | Sleeps: 8

Acorn Point

Easton

Beds: 5 | Baths: 5.5 | Sleeps: 10

Belle Aire Landing

East New Market

Beds: 9 | Baths: 6 | Sleeps: 22

The Water House

St. Michaels

Beds: 5 | Baths: 6 | Sleeps: 9