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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

Flo Farm

Cambridge

Beds: 7 | Baths: 6.5 | Sleeps: 16

Bushey Heath Farm

Royal Oak

Beds: 4 | Baths: 2 | Sleeps: 8

Monasterevin

Cambridge

Beds: 4 | Baths: 3.5 | Sleeps: 10

Bay Water Cottage

Church Creek

Beds: 4 | Baths: 3.5 | Sleeps: 8

Judith's Garden

Oxford

Beds: 4 | Baths: 2.5 | Sleeps: 8

Caulk's Cove

Bozman

Beds: 3 | Baths: 2.5 | Sleeps: 6

Chesapeake Pines

Easton

Beds: 4 | Baths: 4 | Sleeps: 8

Bayberry Cove

Cambridge

Beds: 7 | Baths: 5.5 | Sleeps: 18

Belle Aire Landing

East New Market

Beds: 9 | Baths: 6 | Sleeps: 22

Blue Bay Haven

Stevensville

Beds: 7 | Baths: 5.5 | Sleeps: 18

Cedar Cove on the Miles

Easton

Beds: 4 | Baths: 4 | Sleeps: 8

Nantucket on the Chesapeake

Annapolis

Beds: 4 | Baths: 2.5 | Sleeps: 8

Retreat on Grace Creek

Bozman

Beds: 6 | Baths: 8 | Sleeps: 12

Blue Gates

Easton

Beds: 4 | Baths: 4 | Sleeps: 8

Ben Oaks Drive

Severna Park

Beds: 4 | Baths: 2.5 | Sleeps: 10

Oxford Oasis

Oxford

Beds: 5 | Baths: 7 | Sleeps: 10

Graceful View

Bozman

Beds: 3 | Baths: 2 | Sleeps: 6

Riverview Retreat

Saint Michaels

Beds: 3 | Baths: 2.5 | Sleeps: 6

Sunflower Cottage

Oxford

Beds: 2 | Baths: 1 | Sleeps: 4

Mill Creek

Wye Mills

Beds: 5 | Baths: 3.5 | Sleeps: 10

Crabber's Cove

St. Michaels

Beds: 3 | Baths: 3 | Sleeps: 6

The Landing

Saint Michaels

Beds: 4 | Baths: 3 | Sleeps: 8

Osprey Point

Saint Michaels

Beds: 4 | Baths: 3.5 | Sleeps: 8

The Water House

St. Michaels

Beds: 5 | Baths: 6 | Sleeps: 9

Pines at Barrett Cove

Saint Michaels

Beds: 3 | Baths: 3 | Sleeps: 6