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
View Property
Special Offer! Broadwater View FROM $5800

Broadwater View

Royal Oak
Beds: 5 | Baths: 4.5 | Sleeps: 10
View Property
Holland Point Preserve FROM $4165

Holland Point Preserve

Taylors Island
Beds: 5 | Baths: 5 | Sleeps: 14
View Property
Special Offer! Bayberry Cove FROM $7000

Bayberry Cove

Cambridge
Beds: 7 | Baths: 5.5 | Sleeps: 17
View Property
Special Offer! Simplicity Cottage FROM $1500

Simplicity Cottage

Tilghman
Beds: 2 | Baths: 1.5 | Sleeps: 4
View Property
Nantucket on the Chesapeake FROM $3940 - $12500

Nantucket on the Chesapeake

Annapolis
Beds: 4 | Baths: 3.5 | Sleeps: 10
View Property
Special Offer! Oxford Oasis FROM $4900

Oxford Oasis

Oxford
Beds: 6 | Baths: 7 | Sleeps: 12
View Property
Special Offer! Lee Haven FROM $5250

Lee Haven

Easton
Beds: 5 | Baths: 4.5 | Sleeps: 10
View Property
Special Offer! Sycamore Acres FROM $5850

Sycamore Acres

Easton
Beds: 6 | Baths: 5.5 | Sleeps: 12
View Property
Special Offer! Hudson Manor FROM $6500

Hudson Manor

Cambridge
Beds: 7 | Baths: 6 | Sleeps: 22
View Property
The Bay House on Easy Lane FROM $3800

The Bay House on Easy Lane

Centreville
Beds: 3 | Baths: 3.5 | Sleeps: 8
View Property
Special Offer! Cedar Cove on the Miles FROM $3450

Cedar Cove on the Miles

Easton
Beds: 4 | Baths: 4 | Sleeps: 8
View Property
Special Offer! Pines at Irish Creek FROM $2720

Pines at Irish Creek

Royal Oak
Beds: 4 | Baths: 3 | Sleeps: 8
View Property
Special Offer! Emily's Lane FROM $4500

Emily's Lane

Wittman
Beds: 4 | Baths: 3.5 | Sleeps: 8
View Property
Fairview FROM $12500

Fairview

Easton
Beds: 5 | Baths: 6 | Sleeps: 10
View Property
Special Offer! Chesapeake Pines FROM $2100

Chesapeake Pines

Easton
Beds: 4 | Baths: 4 | Sleeps: 8
View Property
Special Offer! Pride and Joy FROM $1500

Pride and Joy

Oxford
Beds: 3 | Baths: 2 | Sleeps: 6
View Property
Special Offer! Captain's Cove FROM $5625

Captain's Cove

Saint Michaels
Beds: 5 | Baths: 4.5 | Sleeps: 10
View Property
Acorn Point FROM $8500

Acorn Point

Easton
Beds: 5 | Baths: 5.5 | Sleeps: 10
View Property
Special Offer! Heron Point FROM $4250

Heron Point

Royal Oak
Beds: 4 | Baths: 2.5 | Sleeps: 8
View Property
Blue Gates FROM $6370

Blue Gates

Easton
Beds: 4 | Baths: 4 | Sleeps: 8
View Property
Special Offer! Tidal Serenity FROM $2850

Tidal Serenity

Taylors Island
Beds: 5 | Baths: 2.5 | Sleeps: 15
View Property
Special Offer! Caulk's Cove FROM $1890

Caulk's Cove

Bozman
Beds: 3 | Baths: 2.5 | Sleeps: 6
View Property
Special Offer! Memory Lane FROM $1250

Memory Lane

Oxford
Beds: 4 | Baths: 2full, 2 half | Sleeps: 8
View Property
Special Offer! The Water House FROM $3500 - $4200

The Water House

St. Michaels
Beds: 5 | Baths: 5.5 | Sleeps: 9
View Property
Special Offer! Bay Water Cottage FROM $2135

Bay Water Cottage

Church Creek
Beds: 4 | Baths: 3.5 | Sleeps: 8
View Property
Special Offer! At Tricefields Court FROM $4500

At Tricefields Court

Saint Michaels
Beds: 4 | Baths: 5 | Sleeps: 8
View Property
Special Offer! Mallard Point Cottage FROM $2050

Mallard Point Cottage

McDaniel
Beds: 4 | Baths: 3 | Sleeps: 8
View Property
Special Offer! Loblolly Cove FROM $4075

Loblolly Cove

Neavitt
Beds: 4 | Baths: 3 | Sleeps: 8
View Property
22 Fleet Street FROM $2793 - $14000

22 Fleet Street

Annapolis
Beds: 3 | Baths: 2.5 | Sleeps: 6
View Property
East Street Easy Walk FROM $1575 - $2750

East Street Easy Walk

Annapolis
Beds: 1 | Baths: 1.5 | Sleeps: 2
View Property
Special Offer! Crabber's Cove FROM $2400 - $2750

Crabber's Cove

St. Michaels
Beds: 3 | Baths: 3 | Sleeps: 6
View Property
Special Offer! Indian Fields FROM $3500

Indian Fields

Cambridge
Beds: 5 | Baths: 4.5 | Sleeps: 13
View Property
Special Offer! Thornton FROM $4500 - $6000

Thornton

Chestertown
Beds: 6 | Baths: 4.5 | Sleeps: 11
View Property
Duck Cove FROM $1200

Duck Cove

Neavitt
Beds: 2 | Baths: 1 | Sleeps: 4
View Property
Special Offer! Graceful View FROM $2450

Graceful View

Bozman
Beds: 3 | Baths: 2 | Sleeps: 6
View Property
Special Offer! Mill Creek FROM $4750

Mill Creek

Wye Mills
Beds: 5 | Baths: 3.5 | Sleeps: 10
View Property
Special Offer! Swan's Rest FROM $3050

Swan's Rest

Easton
Beds: 3 | Baths: 3 | Sleeps: 6
View Property
Special Offer! Sunrise Cove FROM $3000

Sunrise Cove

Saint Michaels
Beds: 4 | Baths: 3 | Sleeps: 8
View Property
Sunflower Cottage FROM $1250

Sunflower Cottage

Oxford
Beds: 2 | Baths: 1 | Sleeps: 4
View Property
Special Offer! Creek Cottage FROM $4750

Creek Cottage

Centreville
Beds: 4 | Baths: 4 | Sleeps: 10
View Property
Special Offer! Town and Country FROM $4900

Town and Country

Saint Michaels
Beds: 4 | Baths: 3 | Sleeps: 10
View Property
Judith's Garden FROM $4600

Judith's Garden

Oxford
Beds: 4 | Baths: 2.5 | Sleeps: 8
View Property
Special Offer! Osprey Point FROM $3225

Osprey Point

Saint Michaels
Beds: 4 | Baths: 3.5 | Sleeps: 8
View Property
Special Offer! Clearview FROM $2850

Clearview

Tilghman
Beds: 3 | Baths: 3 | Sleeps: 6
View Property
Special Offer! Oxford Beach Cottage FROM $1850

Oxford Beach Cottage

Oxford
Beds: 3 | Baths: 2 | Sleeps: 6
View Property
Special Offer! Carpenter Alley Cottage FROM $1750

Carpenter Alley Cottage

St. Michaels
Beds: 3 | Baths: 3 | Sleeps: 6
View Property
McKendree Street Mainland FROM $3150 - $8500

McKendree Street Mainland

Annapolis
Beds: 4 | Baths: 3 | Sleeps: 8
View Property
PennyWhistle FROM $2750

PennyWhistle

McDaniel
Beds: 4 | Baths: 3 | Sleeps: 8
View Property
Special Offer! Escape Farm FROM $3000

Escape Farm

Royal Oak
Beds: 3 | Baths: 4 | Sleeps: 6
View Property
Special Offer! Pines at Barrett Cove FROM $4025

Pines at Barrett Cove

Saint Michaels
Beds: 3 | Baths: 3 | Sleeps: 6
View Property
Retreat on Grace Creek FROM $11000

Retreat on Grace Creek

Bozman
Beds: 6 | Baths: 8 | Sleeps: 12
View Property
Special Offer! Belle Aire Landing FROM $11900

Belle Aire Landing

East New Market
Beds: 9 | Baths: 6 | Sleeps: 22
View Property
Ben Oaks Drive FROM $5800

Ben Oaks Drive

Severna Park
Beds: 4 | Baths: 2.5 | Sleeps: 10
View Property
Special Offer! Willoughby FROM $5250 - $7750

Willoughby

Cambridge
Beds: 7 | Baths: 6 | Sleeps: 24
View Property
Special Offer! The Landing FROM $4000

The Landing

Saint Michaels
Beds: 4 | Baths: 3 | Sleeps: 8
View Property
Special Offer! Bushey Heath Farm FROM $3500

Bushey Heath Farm

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