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106 Church Alley

1. 106 Church Alley

Historic District townhouse featuring stylish, modern updates offers a home base to unwind or celebrate with family and friends in a beautiful and highly walkable part of town.
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108 Annex

2. 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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114 High Street Vacation Rental

3. 114 High Street Vacation Rental

 Chestertown, Maryland
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200 High Street

4. 200 High Street

 Chestertown, Maryland
Bright and open 2 bedroom apartment in the heart of downtown Chestertown
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Bay Breeze Inn II

5. Bay Breeze Inn II

 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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Bayshore Campground

6. 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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Bayside Cottage

7. Bayside Cottage

 Rock Hall, Maryland
A block off of Rock Hall harbor, Bayside Cottage is a dog-friendly, 3BR/2BA home with a deck, grill, fenced yard, AC, internet/Wi-Fi, fireplace and driveway parking. Walk to restaurants/marinas.
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Bayside Retreat

8. 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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Black Duck Inn

9. 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 1860

10. Brampton 1860

 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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Brittland Manor

11. 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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Carriage House

12. 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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Circa 1865

13. Circa 1865

 Still Pond, Maryland
The Still Pond Inn is a beautiful 1865 farm house with secure entry. Two 3-room suites and one queen room. All rooms feature large screen, streaming TVs, and free Wi Fi. Suites have additional sitting rooms, all rooms and all bathrooms havewalk-in showers
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Comfort Inn & Suites

14. Comfort Inn & Suites

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

15. 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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Coveside Cottage

16. 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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Crow Vineyard, Winery & Inn

17. 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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Downtown Apartment

18. 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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Evergreen Knoll Cottages

19. Evergreen Knoll Cottages

 Betterton, Maryland
Secluded Waterfront Vacation Cottages
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Great Oak Manor

20. Great Oak Manor

 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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