All Properties

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.

Viewing 50 Results

Sort By:

All Properties

Chesapeake Bay Vacation Rentals in the Eastern Shore

Memory Lane

Oxford

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

Pines at Barrett Cove

Saint Michaels

Beds: 3 | Baths: 3 | Sleeps: 6

Windward Cove

Grasonville

Beds: 4 | Baths: 3 | Sleeps: 8

Osprey Point

Saint Michaels

Beds: 4 | Baths: 3.5 | Sleeps: 8

Mallard Point Cottage

McDaniel

Beds: 4 | Baths: 3 | Sleeps: 8

Ben Oaks Drive

Severna Park

Beds: 4 | Baths: 2.5 | Sleeps: 10

Simplicity Cottage

Tilghman

Beds: 2 | Baths: 1.5 | Sleeps: 4

Bay Water Cottage

Church Creek

Beds: 4 | Baths: 3.5 | Sleeps: 8

The Water House

St. Michaels

Beds: 5 | Baths: 6 | Sleeps: 9

Thornton

Chestertown

Beds: 6 | Baths: 4.5 | Sleeps: 13

Pride and Joy

Oxford

Beds: 3 | Baths: 2 | Sleeps: 6

22 Fleet Street

Annapolis

Beds: 3 | Baths: 2.5 | Sleeps: 6

Oxford Oasis

Oxford

Beds: 5 | Baths: 7 | Sleeps: 10

Oxford Beach Cottage

Oxford

Beds: 3 | Baths: 2 | Sleeps: 6

Blue Gates

Easton

Beds: 4 | Baths: 4 | Sleeps: 8

Riverview Retreat

Saint Michaels

Beds: 3 | Baths: 2.5 | Sleeps: 6

Cedar Cove on the Miles

Easton

Beds: 4 | Baths: 4 | Sleeps: 8

Monasterevin

Cambridge

Beds: 4 | Baths: 3.5 | Sleeps: 10

Heron Point

Royal Oak

Beds: 4 | Baths: 2.5 | Sleeps: 8

Judith's Garden

Oxford

Beds: 4 | Baths: 2.5 | Sleeps: 8

The Bird's Nest

Cambridge

Beds: 5 | Baths: 3.5 | Sleeps: 16

Captain's Cove

Saint Michaels

Beds: 5 | Baths: 4.5 | Sleeps: 10

Willoughby

Cambridge

Beds: 7 | Baths: 6 | Sleeps: 24

Caulk's Cove

Bozman

Beds: 3 | Baths: 2.5 | Sleeps: 6

McKendree Street Mainland

Annapolis

Beds: 4 | Baths: 3 | Sleeps: 8

Escape Farm

Royal Oak

Beds: 6 | Baths: 5.5 | Sleeps: 12