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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

Memory Lane

Oxford

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

Captain's Cove

Saint Michaels

Beds: 5 | Baths: 4.5 | Sleeps: 10

Judith's Garden

Oxford

Beds: 4 | Baths: 2.5 | Sleeps: 8

Ben Oaks Drive

Severna Park

Beds: 4 | Baths: 2.5 | Sleeps: 10

Flo Farm

Cambridge

Beds: 7 | Baths: 6.5 | Sleeps: 16

Emily's Lane

Wittman

Beds: 4 | Baths: 3.5 | Sleeps: 8

Osprey Point

Saint Michaels

Beds: 4 | Baths: 3.5 | Sleeps: 8

Caulk's Cove

Bozman

Beds: 3 | Baths: 2.5 | Sleeps: 6

Crabber's Cove

St. Michaels

Beds: 3 | Baths: 3 | Sleeps: 6

Riverview Retreat

Saint Michaels

Beds: 3 | Baths: 2.5 | Sleeps: 6

Clearview

Tilghman

Beds: 3 | Baths: 3 | Sleeps: 6

Monasterevin

Cambridge

Beds: 4 | Baths: 3.5 | Sleeps: 10

Cedar Cove on the Miles

Easton

Beds: 4 | Baths: 4 | Sleeps: 8

Sunflower Cottage

Oxford

Beds: 2 | Baths: 1 | Sleeps: 4

The Water House

St. Michaels

Beds: 5 | Baths: 6 | Sleeps: 8

Chesapeake Pines

Easton

Beds: 4 | Baths: 4 | Sleeps: 8

Blue Bay Haven

Stevensville

Beds: 7 | Baths: 5.5 | Sleeps: 18

Escape Farm

Royal Oak

Beds: 6 | Baths: 5.5 | Sleeps: 12

The Cabin at Broad Creek

Bozman

Beds: 5 | Baths: 3/2 | Sleeps: 10

Pride and Joy

Oxford

Beds: 3 | Baths: 2 | Sleeps: 6

Thornton

Chestertown

Beds: 6 | Baths: 4.5 | Sleeps: 13

Hudson Manor

Cambridge

Beds: 7 | Baths: 6 | Sleeps: 22

Retreat on Grace Creek

Bozman

Beds: 6 | Baths: 8 | Sleeps: 12

Mill Creek

Wye Mills

Beds: 5 | Baths: 3.5 | Sleeps: 10

Acorn Point

Easton

Beds: 5 | Baths: 5.5 | Sleeps: 10

Blue Gates

Easton

Beds: 4 | Baths: 4 | Sleeps: 8