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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

Serenity in St. Michaels

Saint Michaels

Beds: 5 | Baths: 4.5 | Sleeps: 4

Ben Oaks Drive

Severna Park

Beds: 4 | Baths: 2.5 | Sleeps: 10

Simplicity Cottage

Tilghman

Beds: 2 | Baths: 1.5 | Sleeps: 4

Memory Lane

Oxford

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

Retreat on Grace Creek

Bozman

Beds: 6 | Baths: 8 | Sleeps: 12

Captain's Cove

Saint Michaels

Beds: 5 | Baths: 4.5 | Sleeps: 10

Clearview

Tilghman

Beds: 3 | Baths: 3 | Sleeps: 6

Hudson Manor

Cambridge

Beds: 7 | Baths: 6 | Sleeps: 22

Windward Cove

Grasonville

Beds: 4 | Baths: 3 | Sleeps: 8

Leeds Landing

Easton

Beds: 4 | Baths: 3 | Sleeps: 8

Sunrise Cove

Saint Michaels

Beds: 4 | Baths: 3 | Sleeps: 8

Thornton

Chestertown

Beds: 6 | Baths: 4.5 | Sleeps: 11

Bushey Heath Farm

Royal Oak

Beds: 4 | Baths: 2 | Sleeps: 8

Riverview Retreat

Saint Michaels

Beds: 3 | Baths: 2.5 | Sleeps: 6

Judith's Garden

Oxford

Beds: 4 | Baths: 2.5 | Sleeps: 8

Willoughby

Cambridge

Beds: 7 | Baths: 6 | Sleeps: 24

Cedar Cove on the Miles

Easton

Beds: 4 | Baths: 4 | Sleeps: 8

Osprey Point

Saint Michaels

Beds: 4 | Baths: 3.5 | Sleeps: 8

Pride and Joy

Oxford

Beds: 3 | Baths: 2 | Sleeps: 6

Chesapeake Pines

Easton

Beds: 4 | Baths: 4 | Sleeps: 8

Oxford Oasis

Oxford

Beds: 6 | Baths: 7 | Sleeps: 12

Creek Cottage

Centreville

Beds: 4 | Baths: 4 | Sleeps: 10

Acorn Point

Easton

Beds: 5 | Baths: 5.5 | Sleeps: 10

22 Fleet Street

Annapolis

Beds: 3 | Baths: 2.5 | Sleeps: 6

Nantucket on the Chesapeake

Annapolis

Beds: 4 | Baths: 2.5 | Sleeps: 8

Caulk's Cove

Bozman

Beds: 3 | Baths: 2.5 | Sleeps: 6