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Dog Friendly: Yes

Showing 1 - 10 of 39 Eastern Shore Maryland pet friendly lodging.

What is a vacation without your best friend? The Eastern Shore is a very dog friendly environment and over 75% of our homes are pet friendly. Multiple acres, the waterfront, you may even find an occasional dish of water and snack outside our storefronts for your canine friend. Please note that fees and conditions apply to our pet friendly homes, and our policy is dogs only. Do not let another season pass you by!

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Macks Landing

22801 Pot Pie Road
Wittman - Cottage
Bedrooms: 3
Sleeps: 6
Dogs Allowed, Kayak(s) Included, Linens/Towels Provided


This charming property located just outside of St. Michaels has all you need for plug-n-play fun for your family! A playgym, private swimming pool,...more
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Captains Cottage

8978 Glebe Creek Road
Easton - Cottage
Bedrooms: 3
Sleeps: 6
Dogs Allowed, Linens/Towels Provided


This darling well kept waterfront cottage is situated just minutes from historic Easton but on lovely private waterfront on Glebe Creek. Enjoy bright decorating,...more
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Easton Hideaway

8983 Glebe Creek Road
Easton - Cottage
Bedrooms: 3
Sleeps: 6
Dogs Allowed, Linens/Towels Provided


Private dock, newly furnished, gourmet kitchen and just minutes to downtown Easton for theatre, arts, fine dining and shopping, you can have an action packed...more
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Martini Cottage

508 South Morris Street
Oxford - Cottage
Bedrooms: 2
Sleeps: 4
Dogs Allowed, Kayak(s) Included, Linens/Towels Provided


This charming Sears Cottage is located next to Pope's Tavern in the heart of Oxford. Newly furnished, views of the marina from the front...more
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Lovely Cove Farm

23542 Lovely Lane
Chestertown - House
Bedrooms: 4
Sleeps: 11
Dogs Allowed, Kayak(s) Included, Linens/Towels Provided


What do we love the most about this property? The list is long We love the meandering driveway to the shaded 12 acre parcel...more
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Eagle Haven

5939 Horns Point Road
Cambridge - House
Bedrooms: 5
Sleeps: 18
Dogs Allowed, Linens/Towels Provided


Think back to a childhood vacation with your aunts, uncles, grandparents and cousins. Waking up to big breakfasts, running outside and letting your imagination...more
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Colstons Cove Farmhouse

1725 Brannocks Neck Road
Cambridge - House
Bedrooms: 4
Sleeps: 10
Dogs Allowed, Linens/Towels Provided


Situated on over 25 acres, we love this home's privacy with the beautiful waterside pool. The farmhouse renovation provides luxury amidst nature. Incredible views...more
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Crabber's Cove

24611 Long Haul Road
St. Michaels - Cottage
Bedrooms: 3
Sleeps: 6
Dogs Allowed, Kayak(s) Included, Linens/Towels Provided


Comfortably furnished, spruced up and ready for your visit, this cottage is perfectly located for small families or two couples visiting St. Michaels...more
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Pride and Joy Cottage

100 Caroline Street
Oxford - Cottage
Bedrooms: 3
Sleeps: 6
Dogs Allowed, Linens/Towels Provided


Tucked away just as you arrive in the town of Oxford, Pride and Joy is a terrific spot for those looking for a step back...more
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Swans Rest

26577 Arcadia Shores Road
Easton - House
Bedrooms: 3
Sleeps: 6
Dogs Allowed, Kayak(s) Included, Linens/Towels Provided


The Swans Rest vacation home is the "easy button". No surprises, everything upgraded and well decorated. Full onsite amenities - check out the...more
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101 E. Dover Street
Easton, MD 21601


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