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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

Oxford Beach Cottage

Oxford

Beds: 3 | Baths: 2 | Sleeps: 6

East Street Easy Walk

Annapolis

Beds: 1 | Baths: 1.5 | Sleeps: 2

Memory Lane

Oxford

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

Monasterevin

Cambridge

Beds: 4 | Baths: 3.5 | Sleeps: 10

Clearview

Tilghman

Beds: 3 | Baths: 3 | Sleeps: 6

Mallard Point Cottage

McDaniel

Beds: 4 | Baths: 3 | Sleeps: 8

Serenity in St. Michaels

Saint Michaels

Beds: 5 | Baths: 4.5 | Sleeps: 4

Emily's Lane

Wittman

Beds: 4 | Baths: 3.5 | Sleeps: 8

Ben Oaks Drive

Severna Park

Beds: 4 | Baths: 2.5 | Sleeps: 10

Escape Farm

Royal Oak

Beds: 6 | Baths: 5.5 | Sleeps: 12

Bushey Heath Farm

Royal Oak

Beds: 4 | Baths: 2 | Sleeps: 8

Simplicity Cottage

Tilghman

Beds: 2 | Baths: 1.5 | Sleeps: 4

Caulk's Cove

Bozman

Beds: 3 | Baths: 2.5 | Sleeps: 6

Carpenter Alley Cottage

St. Michaels

Beds: 3 | Baths: 3 | Sleeps: 6

Crabber's Cove

St. Michaels

Beds: 3 | Baths: 3 | Sleeps: 6

Flo Farm

Cambridge

Beds: 7 | Baths: 6.5 | Sleeps: 16

Blue Gates

Easton

Beds: 4 | Baths: 4 | Sleeps: 8

Heron Point

Royal Oak

Beds: 4 | Baths: 2.5 | Sleeps: 8

Indian Fields

Cambridge

Beds: 5 | Baths: 4.5 | Sleeps: 13

Creek Cottage at Reed Creek Farm

Centreville

Beds: 4 | Baths: 4 | Sleeps: 10

Graceful View

Bozman

Beds: 3 | Baths: 2 | Sleeps: 6

Judith's Garden

Oxford

Beds: 4 | Baths: 2.5 | Sleeps: 8

Pines at Barrett Cove

Saint Michaels

Beds: 3 | Baths: 3 | Sleeps: 6

Belle Aire Landing

East New Market

Beds: 9 | Baths: 6 | Sleeps: 22

Thorntonwood

Bozman

Beds: 4 | Baths: 2.5 | Sleeps: 8

Bayberry Cove

Cambridge

Beds: 7 | Baths: 5.5 | Sleeps: 18