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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

Bayberry Cove

Cambridge

Beds: 7 | Baths: 5.5 | Sleeps: 18

Serenity in St. Michaels

Saint Michaels

Beds: 5 | Baths: 4.5 | Sleeps: 4

Broadwater View

Royal Oak

Beds: 5 | Baths: 4.5 | Sleeps: 10

Tidal Serenity

Taylors Island

Beds: 5 | Baths: 2.5 | Sleeps: 15

Town and Country

Saint Michaels

Beds: 4 | Baths: 3 | Sleeps: 8

Sunflower Cottage

Oxford

Beds: 2 | Baths: 1 | Sleeps: 4

The Bay House on Easy Lane

Centreville

Beds: 3 | Baths: 3.5 | Sleeps: 8

Escape Farm

Royal Oak

Beds: 3 | Baths: 4 | Sleeps: 6

Simplicity Cottage

Tilghman

Beds: 2 | Baths: 1.5 | Sleeps: 4

Caulk's Cove

Bozman

Beds: 3 | Baths: 2.5 | Sleeps: 6

Acorn Point

Easton

Beds: 5 | Baths: 5.5 | Sleeps: 10

Riverview Retreat

Saint Michaels

Beds: 3 | Baths: 2.5 | Sleeps: 6

McKendree Street Mainland

Annapolis

Beds: 4 | Baths: 3 | Sleeps: 8

Bushey Heath Farm

Royal Oak

Beds: 4 | Baths: 2 | Sleeps: 8

Blue Gates

Easton

Beds: 4 | Baths: 4 | Sleeps: 8

Carpenter Alley Cottage

St. Michaels

Beds: 3 | Baths: 3 | Sleeps: 6

Mill Creek

Wye Mills

Beds: 5 | Baths: 3.5 | Sleeps: 10

Hudson Manor

Cambridge

Beds: 7 | Baths: 6 | Sleeps: 22

Loblolly Cove

Neavitt

Beds: 4 | Baths: 3 | Sleeps: 8

The Bird's Nest

Cambridge

Beds: 5 | Baths: 3.5 | Sleeps: 16

Cedar Cove on the Miles

Easton

Beds: 4 | Baths: 4 | Sleeps: 8

Pines at Barrett Cove

Saint Michaels

Beds: 3 | Baths: 3 | Sleeps: 6

22 Fleet Street

Annapolis

Beds: 3 | Baths: 2.5 | Sleeps: 6

Graceful View

Bozman

Beds: 3 | Baths: 2 | Sleeps: 6

Duck Cove

Neavitt

Beds: 2 | Baths: 1 | Sleeps: 4

Heron Point

Royal Oak

Beds: 4 | Baths: 2.5 | Sleeps: 8