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Dog Friendly: Yes

Showing 1 - 10 of 40 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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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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Gladimere Glad I'm Here""

27922 Tred Avon Drive
Easton - Cottage
Bedrooms: 3
Sleeps: 8
Dogs Allowed, Kayak(s) Included, Linens/Towels Provided


Perfectly located between Oxford and Easton - Gladimere is nestled on 3 1/2 acres of private waterfront but minutes to the best that each...more
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Kamp Kolohe - Ko-Lo-Hey""

22741 Marshall Lane
Wittman - Cottage
Bedrooms: 3
Sleeps: 5
Dogs Allowed, Linens/Towels Provided


In Hawaiian, Kalohe means mischievous, rascal and naughty. Fitting term for this cottages as its casual decor speaks of the islands and a more...more
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Duck Cove Cottage

6398 Duck Cove Lane
Neavitt - Cottage
Bedrooms: 2
Sleeps: 4
Dogs Allowed, Kayak(s) Included, Linens/Towels Provided


This little gem sits at the end of Duck Cove Lane in heart of Neavitt Village and 10 miles from St. Michaels. If...more
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Simplicity Cottage

5447 Rude Ave
Tilghman Island - Cottage
Bedrooms: 2
Sleeps: 4
Dogs Allowed, Linens/Towels Provided


This fantastic 1920's Waterman's cottage has the charm and waterfront location that is hard to come by these days. Restored to give you some...more
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Pines at Barrett Cove

7149 Drum Point Road
St. Michaels - Cottage
Bedrooms: 3
Sleeps: 6
Dogs Allowed, Kayak(s) Included, Linens/Towels Provided


One of our most popular houses, Pines at Barrett Cove offers virtually everything you need for your next vacation. A gourmet kitchen and spacious...more
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Heron Point

25680 Edgeview Road
Royal Oak - Cottage
Bedrooms: 4
Sleeps: 9
Dogs Allowed, Linens/Towels Provided


Perched on over 3 acres of waterfront this unassuming quaint cottage packs a punch. A true point of land with water on three sides and...more
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Magnolia Cottage

218 North Morris Unit B
Oxford - Cottage
Bedrooms: 2
Sleeps: 4
Dogs Allowed


Resting underneath the protective Magnolia Canopy this aptly named 1890s condo/cottage is the antidote to escaping the city or suburbs. Nestled in the heart...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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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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101 E. Dover Street
Easton, MD 21601


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