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108 Annex

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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200 High Street

2. 200 High Street

 Chestertown, Maryland
Bright and open 2 bedroom apartment in the heart of downtown Chestertown
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Bayside Retreat

3. 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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Cottage On Kent

4. 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

5. 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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Downtown Apartment

6. 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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InnTowne House

7. InnTowne House

 Rock Hall, Maryland
Upscale, modern and new two bedroom apartment overlooking Main St. in Rock Hall. Wonderful amenities, lots of space and full kitchen. $275 per night. Up to four guests. Two night minimum, weekly rates available. Includes breakfast at Java Rock.
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Pilot House

8. Pilot House

 Rock Hall, Maryland
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River Lodge

9. River Lodge

 Chestertown, Maryland
With its rustic, peaceful waterfront setting, the River Lodge is an excellent venue for a business retreat, private getaway, family reunion, or informal wedding; a four season destination.
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Rolling View Farms, LLC

10. Rolling View Farms, LLC

 Chestertown, Maryland
Please consider staying with us when visiting historic Chestertown. Our five year young Rancher is ideally located within walking distance to Washington College and downtown. This fully equipped home offers the perfect getaway.
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Ruby's Sea Glass Cottage LLC

11. Ruby's Sea Glass Cottage LLC

 Betterton, Maryland
Vacation Rental House in Betterton, MD
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Sharp Street Retreat

12. Sharp Street Retreat

 Rock Hall, Maryland
This charming home on Sharp Street in Rock Hall is a perfect place to stay for you and your family and friends. This recently renovated house sleeps 10 comfortably..
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Stepne Manor

13. Stepne Manor

 Chestertown, Maryland
This historic circa 1690 manor house with wide covered porch is within walking distance to downtown Chestertown. An ideal location for small retreats, meetings and town charm weddings.
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Sunset Lodge

14. Sunset Lodge

 Rock Hall, Maryland
58-acre estate located on the Chesapeake Bay with a personal beach, offering stunning waterfront views and sunsets. Only 3 miles away from town and Eastern Neck Island.
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Swan Creek Waterfront

15. Swan Creek Waterfront

 Rock Hall, Maryland
Swan Creek Waterfront Cottage with large yard leading to 200'+ pier for boats, crabbing, and fishing. Explore the quaint town of Rock Hall with nearby restaurants, shopping and loads of outdoor activities.
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The Beach Cottage

16. The Beach Cottage

 Rock Hall, Maryland
Beach Front Cottage Get-A-Way Newly renovated, charming cottage with a sandy beach right across the quiet street. Beach is great for swimming, kayaking or just gazing at the boats passing by in the distance. Amazing Chesapeake Bay sunsets in the quai
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The Lodge on Main

17. The Lodge on Main

 Rock Hall, Maryland
Everything is crisp, clean and recently renovated. It sleeps up to 9 in three bedrooms and offers 2 full baths. The completely efficient kitchen offers an overlook on Main Street.
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Thornton Estate

18. 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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Tipsea Crab

19. Tipsea Crab

 Rock Hall, Maryland
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Welcome Aboard

20. Welcome Aboard

 Rock Hall, Maryland
Welcome Aboard is a 3 bedroom and 2 1/2 bath home in Rock Hall's Harbor Woods Community. A short walk to Main Street attractions and waterfront dining. Includes Wi-fi, linens, fully equipped kitchen, BBQ, and laundry. Fireplace in living room.

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

400 High Street, 3rd Floor
Chestertown, MD 21620
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