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Bay Breeze Inn

1. Bay Breeze Inn

 Rock Hall, Maryland
Guests savor the unhurried timeless quality of this rural watermen's village where an earlier and friendlier way of life continues to thrive. Guests are invited to enjoy breakfast al fresco on the rear patio or to simply view the garden.
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Black Duck Inn

2. Black Duck Inn

 Rock Hall, Maryland
Overlooking picturesque Rock Hall Harbor, we offer five comfortable guest rooms and complimentary dockage for overnight guests arriving by boat.
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Brampton Bed and Breakfast Inn

3. Brampton Bed and Breakfast Inn

 Chestertown, Maryland
Discover a historic and award-winning bed and breakfast in Chestertown, MD. This romantic inn is situated on 35 beautiful acres with glorious views and delicious breakfasts! Unforgettable rooms offer whirlpool tubs, fireplaces, and flat-screen TVs.
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Carriage House

4. Carriage House

 Rock Hall, Maryland
A delightfully intimate hideaway vacation spot in a quaint fishing village near the Chesapeake Bay. Enjoy stunning water views while being close to great restaurants and quaint shops. We are just a hop, skip and a splash from the Public Beach.
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Crow Vineyard, Winery & Inn

5. Crow Vineyard, Winery & Inn

Sip Stay See Savor
 Kennedyville, Maryland
Enjoy a unique farm experience: walk the trails on our 365 acre farm, enjoy views of the vineyard, experience a wine tasting, stay in our Inn...about an hour from Philadelphia, Baltimore, Washington DC, minutes from Chestertown.
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Great Oak Manor

6. Great Oak Manor

 Chestertown, Maryland
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Haven Point Inn and Gallery

7. Haven Point Inn and Gallery

 Rock Hall, Maryland
Haven Point Inn & Gallery is a new contemporary inn and gallery with beautifully appointed rooms designed with your comfort in mind. A complimentary delicious gourmet breakfast will help you start your day.
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Inn at Haven Harbour

8. Inn at Haven Harbour

 Rock Hall, Maryland
A premier Chesapeake Bay resort destination located in Rock Hall, Maryland. Explore our six buildings, 22 well-appointed guest rooms and suites, full-house vacation rental, pet-friendly accommodations and countless amenities.
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Inn at Huntingfield Creek

9. Inn at Huntingfield Creek

 Rock Hall, Maryland
A true wildlife habitat at this elegant, four-season farm estate with 1100 ft. of glorious waterfront. First class accommodations and full country breakfast. Lovely gardens, walking paths and inviting saltwater pool. Pet and family friendly cottages
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Inn at Mitchell House

10. Inn at Mitchell House

 Chestertown, Maryland
Beauty undisturbed. Historic manor offers a tranquil retreat. Approximately 10 miles outside of Chestertown.
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Inn at Osprey Point, Marina, and Restaurant

11. Inn at Osprey Point, Marina, and Restaurant

 Rock Hall, Maryland
At Osprey Point Inn, Restaurant and Marina, you'll experience the perfect fusion of luxurious accommodations, elegant dining, and a relaxed and friendly environment.
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Kitty Knight Inn

12. Kitty Knight Inn

 Galena, Maryland
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Rolph's Wharf, The River Inn

13. Rolph's Wharf, The River Inn

 Chestertown, Maryland
Spend a night – or a weekend – in charm and comfort. With views of the Chester River and the adjoining farm, the River Inn at Rolph’s Wharf offers you the opportunity to spend a relaxing night or two away from the everyday. Each of the rooms has its
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Spring Cove Manor

14. Spring Cove Manor

 Rock Hall, Maryland
A delightfully secluded B & B at water's edge a short distance from the quaint little fishing village of Rock Hall. Luxurious accommodations in delightful seclusion with kayak and sailing adventures at your doorstep.
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Thornton Estate

15. Thornton Estate

 Chestertown, Maryland
Elegance and seclusion on 300+ acres - Thornton Estate, established in 1664, is a quintessential Eastern Shore estate. The magnificient manor house anchors the 325 acre preserved farm minutes outside of Chestertown, MD.
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White Swan Tavern

16. White Swan Tavern

 Chestertown, Maryland

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Contact
Phone: 410-778-0416
tourism@kentgov.org 

400 High Street, 3rd Floor
Chestertown, MD 21620
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