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 56 Results


Sort By:


Thornton

Chestertown
Beds: 6 | Baths: 4.5 | Sleeps: 11
View Property

Captain's Cove

Saint Michaels
Beds: 5 | Baths: 4.5 | Sleeps: 10
View Property

Sunrise Cove

Saint Michaels
Beds: 4 | Baths: 3 | Sleeps: 8
View Property

Hudson Manor

Cambridge
Beds: 7 | Baths: 6 | Sleeps: 22
View Property

Indian Fields

Cambridge
Beds: 5 | Baths: 4.5 | Sleeps: 13
View Property

Crabber's Cove

St. Michaels
Beds: 3 | Baths: 3 | Sleeps: 6
View Property

Ben Oaks Drive

Severna Park
Beds: 4 | Baths: 2.5 | Sleeps: 10
View Property

East Street Easy Walk

Annapolis
Beds: 1 | Baths: 1.5 | Sleeps: 2
View Property

Broadwater View

Royal Oak
Beds: 5 | Baths: 4.5 | Sleeps: 10
View Property

The Landing

Saint Michaels
Beds: 4 | Baths: 3 | Sleeps: 8
View Property

Tidal Serenity

Taylors Island
Beds: 5 | Baths: 2.5 | Sleeps: 15
View Property

Windward Cove

Grasonville
Beds: 4 | Baths: 3 | Sleeps: 8
View Property

Loblolly Cove

Neavitt
Beds: 4 | Baths: 3 | Sleeps: 8
View Property

Escape Farm

Royal Oak
Beds: 3 | Baths: 4 | Sleeps: 6
View Property

The Water House

St. Michaels
Beds: 5 | Baths: 6 | Sleeps: 9
View Property

Caulk's Cove

Bozman
Beds: 3 | Baths: 2.5 | Sleeps: 6
View Property

Sunflower Cottage

Oxford
Beds: 2 | Baths: 1 | Sleeps: 4
View Property

Pride and Joy

Oxford
Beds: 3 | Baths: 2 | Sleeps: 6
View Property

Creek Cottage

Centreville
Beds: 4 | Baths: 4 | Sleeps: 10
View Property

22 Fleet Street

Annapolis
Beds: 3 | Baths: 2.5 | Sleeps: 6
View Property

At Tricefields Court

Saint Michaels
Beds: 4 | Baths: 5 | Sleeps: 8
View Property

Retreat on Grace Creek

Bozman
Beds: 6 | Baths: 8 | Sleeps: 12
View Property

Judith's Garden

Oxford
Beds: 4 | Baths: 2.5 | Sleeps: 8
View Property

Town and Country

Saint Michaels
Beds: 4 | Baths: 3 | Sleeps: 8
View Property

Cedar Cove on the Miles

Easton
Beds: 4 | Baths: 4 | Sleeps: 8
View Property

Willoughby

Cambridge
Beds: 7 | Baths: 6 | Sleeps: 24
View Property

Bay Water Cottage

Church Creek
Beds: 4 | Baths: 3.5 | Sleeps: 8
View Property

Waverly

Easton
Beds: 5 | Baths: 5.5 | Sleeps: 10
View Property

Acorn Point

Easton
Beds: 5 | Baths: 5.5 | Sleeps: 10
View Property

Monasterevin

Cambridge
Beds: 4 | Baths: 3.5 | Sleeps: 10
View Property

Belle Aire Landing

East New Market
Beds: 9 | Baths: 6 | Sleeps: 22
View Property

Pines at Barrett Cove

Saint Michaels
Beds: 3 | Baths: 3 | Sleeps: 6
View Property

Mallard Point Cottage

McDaniel
Beds: 4 | Baths: 3 | Sleeps: 8
View Property

Bayberry Cove

Cambridge
Beds: 7 | Baths: 5.5 | Sleeps: 18
View Property

McKendree Street Mainland

Annapolis
Beds: 4 | Baths: 3 | Sleeps: 8
View Property

Clearview

Tilghman
Beds: 3 | Baths: 3 | Sleeps: 6
View Property

Blue Gates

Easton
Beds: 4 | Baths: 4 | Sleeps: 8
View Property

Heron Point

Royal Oak
Beds: 4 | Baths: 2.5 | Sleeps: 8
View Property

Oxford Oasis

Oxford
Beds: 6 | Baths: 7 | Sleeps: 12
View Property

Sycamore Acres

Easton
Beds: 6 | Baths: 5.5 | Sleeps: 12
View Property

Graceful View

Bozman
Beds: 3 | Baths: 2 | Sleeps: 6
View Property

Bushey Heath Farm

Royal Oak
Beds: 4 | Baths: 2 | Sleeps: 8
View Property

Mill Creek

Wye Mills
Beds: 5 | Baths: 3.5 | Sleeps: 10
View Property

Simplicity Cottage

Tilghman
Beds: 2 | Baths: 1.5 | Sleeps: 4
View Property

Chesapeake Pines

Easton
Beds: 4 | Baths: 4 | Sleeps: 8
View Property

Duck Cove

Neavitt
Beds: 2 | Baths: 1 | Sleeps: 4
View Property

Nantucket on the Chesapeake

Annapolis
Beds: 4 | Baths: 2.5 | Sleeps: 8
View Property

Emily's Lane

Wittman
Beds: 4 | Baths: 3.5 | Sleeps: 8
View Property

Serenity in St. Michaels

Saint Michaels
Beds: 5 | Baths: 4.5 | Sleeps: 4
View Property

Riverview Retreat

Saint Michaels
Beds: 3 | Baths: 2.5 | Sleeps: 6
View Property

Memory Lane

Oxford
Beds: 4 | Baths: 2full, 2 half | Sleeps: 8
View Property

Oxford Beach Cottage

Oxford
Beds: 3 | Baths: 2 | Sleeps: 6
View Property

The Bird's Nest

Cambridge
Beds: 5 | Baths: 3.5 | Sleeps: 16
View Property

Carpenter Alley Cottage

St. Michaels
Beds: 3 | Baths: 3 | Sleeps: 6
View Property

The Bay House on Easy Lane

Centreville
Beds: 3 | Baths: 3.5 | Sleeps: 8
View Property

Osprey Point

Saint Michaels
Beds: 4 | Baths: 3.5 | Sleeps: 8
View Property