A dog running through the yard at a pet-friendly vacation rental on the Eastern Shore of MD

Pet-Friendly Homes

If you’re a pet owner, then you might be familiar with the dreadful feeling of leaving your loyal pal behind for vacation. Don’t worry — we’ll make sure that you never have to say no to those cute, puppy-dog eyes again. Save money on a kennel and bring your furry friend along with you this year to one of our pet-friendly vacation rentals on the Eastern Shore of MD! They come with excellent amenities as well as plenty of space for your pet to run around. Many of our Chesapeake Bay pet-friendly vacation homes on the Eastern Shore even have large yards that are perfect for tossing the frisbee or playing fetch together!

Did we mention that there are no pet fees with Eastern Shore Vacation Rentals? It’s true — and the list of benefits continues on and on. Take the next step toward a wag-worthy vacation by exploring the Chesapeake Bay pet-friendly properties below. We know you’ll find the perfect retreat for everyone in your family — including your pet, of course!

View Our Pet-Friendly Vacation Rentals on the Eastern Shore of MD

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Pride and Joy FROM $1500

Pride and Joy

Oxford
Beds: 3 | Baths: 2 | Sleeps: 6
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The Bay House on Easy Lane FROM $3800

The Bay House on Easy Lane

Centreville
Beds: 3 | Baths: 3.5 | Sleeps: 8
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Simplicity Cottage FROM $1500

Simplicity Cottage

Tilghman
Beds: 2 | Baths: 1.5 | Sleeps: 4
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East Street Easy Walk FROM $1050 - $2750

East Street Easy Walk

Annapolis
Beds: 1 | Baths: 1.5 | Sleeps: 3
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Duck Cove FROM $1200

Duck Cove

Neavitt
Beds: 2 | Baths: 1 | Sleeps: 4
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Tidal Serenity FROM $2850

Tidal Serenity

Taylors Island
Beds: 5 | Baths: 2.5 | Sleeps: 15
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Chesapeake Pines FROM $2100

Chesapeake Pines

Easton
Beds: 4 | Baths: 4 | Sleeps: 8
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Willoughby FROM $5250 - $7750

Willoughby

Cambridge
Beds: 7 | Baths: 6 | Sleeps: 24
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Town and Country FROM $4900

Town and Country

Saint Michaels
Beds: 4 | Baths: 3 | Sleeps: 10
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Mallard Point Cottage FROM $2050

Mallard Point Cottage

McDaniel
Beds: 4 | Baths: 3 | Sleeps: 8
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Graceful View FROM $2450

Graceful View

Bozman
Beds: 3 | Baths: 2 | Sleeps: 6
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Bushey Heath Farm FROM $3500

Bushey Heath Farm

Royal Oak
Beds: 4 | Baths: 2 | Sleeps: 8
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Memory Lane FROM $1250

Memory Lane

Oxford
Beds: 4 | Baths: 2full, 2 half | Sleeps: 8
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Thornton FROM $4500 - $6000

Thornton

Chestertown
Beds: 6 | Baths: 4.5 | Sleeps: 11
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Carpenter Alley Cottage FROM $1750

Carpenter Alley Cottage

St. Michaels
Beds: 3 | Baths: 3 | Sleeps: 6
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Pines at Barrett Cove FROM $4025

Pines at Barrett Cove

Saint Michaels
Beds: 3 | Baths: 3 | Sleeps: 6
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Osprey Point FROM $3225

Osprey Point

Saint Michaels
Beds: 4 | Baths: 3.5 | Sleeps: 8
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Sycamore Acres FROM $5850

Sycamore Acres

Easton
Beds: 6 | Baths: 5.5 | Sleeps: 12
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Pines at Irish Creek FROM $2720

Pines at Irish Creek

Royal Oak
Beds: 4 | Baths: 3 | Sleeps: 8
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Clearview FROM $2850

Clearview

Tilghman
Beds: 3 | Baths: 3 | Sleeps: 6
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Holland Point Preserve FROM $4165

Holland Point Preserve

Taylors Island
Beds: 5 | Baths: 5 | Sleeps: 14
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Broadwater View FROM $5800

Broadwater View

Royal Oak
Beds: 5 | Baths: 4.5 | Sleeps: 10
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Hudson Manor FROM $6500

Hudson Manor

Cambridge
Beds: 7 | Baths: 6 | Sleeps: 22
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Heron Point FROM $4250

Heron Point

Royal Oak
Beds: 4 | Baths: 2.5 | Sleeps: 8
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Sunrise Cove FROM $3000

Sunrise Cove

Saint Michaels
Beds: 4 | Baths: 3 | Sleeps: 8
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Indian Fields FROM $3500

Indian Fields

Cambridge
Beds: 5 | Baths: 4.5 | Sleeps: 13
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The Water House FROM $3500 - $4200

The Water House

Easton
Beds: 5 | Baths: 5.5 | Sleeps: 9
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Caulk's Cove FROM $1890

Caulk's Cove

Bozman
Beds: 3 | Baths: 2.5 | Sleeps: 6
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Creek Cottage FROM $4750

Creek Cottage

Centreville
Beds: 4 | Baths: 4 | Sleeps: 10
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Escape Farm FROM $3000

Escape Farm

Royal Oak
Beds: 3 | Baths: 4 | Sleeps: 6
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Swan's Rest FROM $3050

Swan's Rest

Easton
Beds: 3 | Baths: 3 | Sleeps: 6
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Bayberry Cove FROM $7000

Bayberry Cove

Cambridge
Beds: 7 | Baths: 5.5 | Sleeps: 17
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Crabber's Cove FROM $2400 - $2750

Crabber's Cove

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