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Search results; Over 1,000 places

Guest favorite
Home in Rock Hall
Waterfront w/upper sundeck and kayaks/paddleboad
8 beds
Apr 1 – 6
5.0 out of 5 average rating, 7 reviews
Guest favorite
Home in Chester
Chester Delight- Fireplace/Deck&Patio+fenced yard
6 beds
Apr 15 – 20
5.0 out of 5 average rating, 38 reviews
Guest favorite
Guest suite in Grasonville
Heron's Haven
Apr 7 – 12
5.0 out of 5 average rating, 8 reviews
Guest favorite
Cottage in Stevensville
Cozy, Waterfront Getaway “The Great Nest”
5 beds
Apr 10 – 15
4.93 out of 5 average rating, 15 reviews
Guest favorite
Home in Stevensville
Cozy home with Screened Porch, Min from Weddings
4 beds
Apr 7 – 12
4.98 out of 5 average rating, 52 reviews
Home in Queenstown
Gorgeous Creek Side Ranch-Style Estate With Dock
6 beds
Apr 1 – 6
New place to stay
Guest favorite
Home in Rock Hall
Cozy 1920's Bungalow Near Water/Local Attractions
4 beds
Apr 1 – 6
5.0 out of 5 average rating, 63 reviews
Guest favorite
Home in Stevensville
1969 Brick Rancher - Kent Island
3 beds
Apr 1 – 6
5.0 out of 5 average rating, 11 reviews
Guest favorite
Home in Stevensville
25-50% Off~Private Beach~Hot Tub~Fire Table~
5 beds
Apr 21 – 26
4.95 out of 5 average rating, 40 reviews
Guest favorite
Home in Stevensville
The Kent Island House
4 beds
Apr 9 – 14
4.97 out of 5 average rating, 95 reviews
Guest favorite
Guest suite in Stevensville
Kent Island Haven - A Waterfront Getaway
1 queen bed
Apr 1 – 6
4.97 out of 5 average rating, 144 reviews
Guest favorite
Houseboat in Stevensville
Chesapeake Houseboat Getaway
3 beds
Apr 14 – 19
4.96 out of 5 average rating, 26 reviews
Guest favorite
Guesthouse in Glen Burnie
The Crab House - a Private, Waterfront Guest House
1 queen bed
Apr 7 – 12
4.94 out of 5 average rating, 259 reviews
Guest favorite
Guesthouse in Grasonville
Eastern Shore Charm on Winchester Creek
1 queen bed
Apr 1 – 6
4.9 out of 5 average rating, 202 reviews
Guest favorite
Home in Arnold
Bring A Boat! Waterfront home-w/basement apt+dock!
2 beds
Apr 1 – 6
4.93 out of 5 average rating, 43 reviews
Guest favorite
Guesthouse in Stevensville
Chesapeake Cottage
3 beds
Apr 15 – 20
5.0 out of 5 average rating, 23 reviews
Guest favorite
Home in Pasadena
Waterfront CHeerful 2 with Private home
2 beds
Apr 11 – 16
5.0 out of 5 average rating, 12 reviews
Home in Stevensville
Incredible home with Panoramic Chesapeake Bay view
7 beds
May 6 – 11