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1. 108 Annex

 Chestertown, Maryland
Welcome to 108Annex, your ideal Chesapeake Bay retreat! Nestled in historic downtown Chestertown. Just steps away from downtown restaurants, cafes, and shops, you'll be able to explore all the Arts & Entertainment District has to offer.
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2. 200 High Street

 Chestertown, Maryland
Bright and open 2 bedroom apartment in the heart of downtown Chestertown
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3. 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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4. Bayshore Campground

 Rock Hall, Maryland
Bayshore Campground is located on the Chesapeake Bay in Rock Hall Maryland, where we offer a beautiful and unique vacation location. Accommodations with water and electric hook-ups available. Come enjoy our peaceful and relaxing atmosphere for all.
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5. Bayside Retreat

 Rock Hall, Maryland
Bayside Retreat has 3 bedrooms and 1 1/2 baths and is located a short walk away from great restaurants on the harbor. Guests also enjoy pool privileges at Rock Hall Landing Marina just 50 yards away.
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6. 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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7. 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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8. Brittland Manor

 Chestertown, Maryland
From fields to rivers Brittland Estates personifies elegance in a rural setting. Our collection of heritage properties are near historic Chestertown and are ideal for weddings, family reunions, corporate events and get-aways.
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9. 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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10. Comfort Inn & Suites

 Chestertown, Maryland
Modern convenience with 81 rooms. Close to Chestertown's Historic District. Breakfast is complimentary.
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11. Cottage On Kent

 Chestertown, Maryland
Cottage On Kent is a charming guest cottage rental. It is located within walking distance to downtown, the Chester River and Washington College.
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12. Coveside Cottage

 Rock Hall, Maryland
A fully equipped home for the most discerning guests. This brand-new home-away-from home supplies every amenity one could demand. Two bedrooms, 2 full baths with skylights, a full kitchen, dining nook, living room opening onto a full deck.
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13. 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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14. Downtown Apartment

 Chestertown, Maryland
1 Bedroom Apartment 2 blocks from downtown Chestertown MD on a quiet residential street with one queen size bed.
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15. Great Oak Manor

 Chestertown, Maryland
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16. 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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17. 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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18. 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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19. Inn at Mitchell House

 Chestertown, Maryland
Beauty undisturbed. Historic manor offers a tranquil retreat. Approximately 10 miles outside of Chestertown.
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20. 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.