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 57 Results

Sort By:

Waverly

Easton

Beds: 5 | Baths: 5.5 | Sleeps: 10

Broadwater View

FROM $5800

Broadwater View

Royal Oak

Beds: 5 | Baths: 4.5 | Sleeps: 10

Holland Point Preserve

FROM $4165

Holland Point Preserve

Taylors Island

Beds: 5 | Baths: 5 | Sleeps: 14

FROM $7000

Bayberry Cove

Cambridge

Beds: 7 | Baths: 5.5 | Sleeps: 17

Simplicity Cottage

FROM $1500

Simplicity Cottage

Tilghman

Beds: 2 | Baths: 1.5 | Sleeps: 4

Nantucket on the Chesapeake

FROM $3940 - $12500

Nantucket on the Chesapeake

Annapolis

Beds: 4 | Baths: 3.5 | Sleeps: 10

FROM $4900

Oxford Oasis

Oxford

Beds: 6 | Baths: 7 | Sleeps: 12

FROM $5250

Lee Haven

Easton

Beds: 5 | Baths: 4.5 | Sleeps: 10

FROM $5850

Sycamore Acres

Easton

Beds: 6 | Baths: 5.5 | Sleeps: 12

FROM $6500

Hudson Manor

Cambridge

Beds: 7 | Baths: 6 | Sleeps: 22

The Bay House on Easy Lane

FROM $3800

The Bay House on Easy Lane

Centreville

Beds: 3 | Baths: 3.5 | Sleeps: 8

Cedar Cove on the Miles

FROM $3450

Cedar Cove on the Miles

Easton

Beds: 4 | Baths: 4 | Sleeps: 8

Pines at Irish Creek

FROM $2720

Pines at Irish Creek

Royal Oak

Beds: 4 | Baths: 3 | Sleeps: 8

FROM $4500

Emily's Lane

Wittman

Beds: 4 | Baths: 3.5 | Sleeps: 8

FROM $12500

Fairview

Easton

Beds: 5 | Baths: 6 | Sleeps: 10

Chesapeake Pines

FROM $2100

Chesapeake Pines

Easton

Beds: 4 | Baths: 4 | Sleeps: 8

FROM $1500

Pride and Joy

Oxford

Beds: 3 | Baths: 2 | Sleeps: 6

FROM $5625

Captain's Cove

Saint Michaels

Beds: 5 | Baths: 4.5 | Sleeps: 10

FROM $8500

Acorn Point

Easton

Beds: 5 | Baths: 5.5 | Sleeps: 10

FROM $4250

Heron Point

Royal Oak

Beds: 4 | Baths: 2.5 | Sleeps: 8

FROM $6370

Blue Gates

Easton

Beds: 4 | Baths: 4 | Sleeps: 8

FROM $2850

Tidal Serenity

Taylors Island

Beds: 5 | Baths: 2.5 | Sleeps: 15

FROM $1890

Caulk's Cove

Bozman

Beds: 3 | Baths: 2.5 | Sleeps: 6

FROM $1250

Memory Lane

Oxford

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

The Water House

FROM $3500 - $4200

The Water House

St. Michaels

Beds: 5 | Baths: 5.5 | Sleeps: 9

Bay Water Cottage

FROM $2135

Bay Water Cottage

Church Creek

Beds: 4 | Baths: 3.5 | Sleeps: 8

At Tricefields Court

FROM $4500

At Tricefields Court

Saint Michaels

Beds: 4 | Baths: 5 | Sleeps: 8

Mallard Point Cottage

FROM $2050

Mallard Point Cottage

McDaniel

Beds: 4 | Baths: 3 | Sleeps: 8

FROM $4075

Loblolly Cove

Neavitt

Beds: 4 | Baths: 3 | Sleeps: 8

22 Fleet Street

FROM $2793 - $14000

22 Fleet Street

Annapolis

Beds: 3 | Baths: 2.5 | Sleeps: 6

East Street Easy Walk

FROM $1575 - $2750

East Street Easy Walk

Annapolis

Beds: 1 | Baths: 1.5 | Sleeps: 2

FROM $2400 - $2750

Crabber's Cove

St. Michaels

Beds: 3 | Baths: 3 | Sleeps: 6

FROM $3500

Indian Fields

Cambridge

Beds: 5 | Baths: 4.5 | Sleeps: 13

FROM $4500 - $6000

Thornton

Chestertown

Beds: 6 | Baths: 4.5 | Sleeps: 11

FROM $1200

Duck Cove

Neavitt

Beds: 2 | Baths: 1 | Sleeps: 4

FROM $2450

Graceful View

Bozman

Beds: 3 | Baths: 2 | Sleeps: 6

FROM $4750

Mill Creek

Wye Mills

Beds: 5 | Baths: 3.5 | Sleeps: 10

FROM $3050

Swan's Rest

Easton

Beds: 3 | Baths: 3 | Sleeps: 6

FROM $3000

Sunrise Cove

Saint Michaels

Beds: 4 | Baths: 3 | Sleeps: 8

Sunflower Cottage

FROM $1250

Sunflower Cottage

Oxford

Beds: 2 | Baths: 1 | Sleeps: 4

FROM $4750

Creek Cottage

Centreville

Beds: 4 | Baths: 4 | Sleeps: 10

Town and Country

FROM $4900

Town and Country

Saint Michaels

Beds: 4 | Baths: 3 | Sleeps: 10

Judith's Garden

FROM $4600

Judith's Garden

Oxford

Beds: 4 | Baths: 2.5 | Sleeps: 8

FROM $3225

Osprey Point

Saint Michaels

Beds: 4 | Baths: 3.5 | Sleeps: 8

FROM $2850

Clearview

Tilghman

Beds: 3 | Baths: 3 | Sleeps: 6

Oxford Beach Cottage

FROM $1850

Oxford Beach Cottage

Oxford

Beds: 3 | Baths: 2 | Sleeps: 6

Carpenter Alley Cottage

FROM $1750

Carpenter Alley Cottage

St. Michaels

Beds: 3 | Baths: 3 | Sleeps: 6

McKendree Street Mainland

FROM $3150 - $8500

McKendree Street Mainland

Annapolis

Beds: 4 | Baths: 3 | Sleeps: 8

FROM $2750

PennyWhistle

McDaniel

Beds: 4 | Baths: 3 | Sleeps: 8

FROM $3000

Escape Farm

Royal Oak

Beds: 3 | Baths: 4 | Sleeps: 6

Pines at Barrett Cove

FROM $4025

Pines at Barrett Cove

Saint Michaels

Beds: 3 | Baths: 3 | Sleeps: 6

Retreat on Grace Creek

FROM $11000

Retreat on Grace Creek

Bozman

Beds: 6 | Baths: 8 | Sleeps: 12

Belle Aire Landing

FROM $11900

Belle Aire Landing

East New Market

Beds: 9 | Baths: 6 | Sleeps: 22

FROM $5800

Ben Oaks Drive

Severna Park

Beds: 4 | Baths: 2.5 | Sleeps: 10

FROM $5250 - $7750

Willoughby

Cambridge

Beds: 7 | Baths: 6 | Sleeps: 24

FROM $4000

The Landing

Saint Michaels

Beds: 4 | Baths: 3 | Sleeps: 8

Bushey Heath Farm

FROM $3500

Bushey Heath Farm

Royal Oak

Beds: 4 | Baths: 2 | Sleeps: 8