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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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114 High Street Vacation Rental

2. 114 High Street Vacation Rental

 Chestertown, Maryland
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200 High Street

3. 200 High Street

 Chestertown, Maryland
Bright and open 2 bedroom apartment in the heart of downtown Chestertown
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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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Downtown Apartment

5. 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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River Lodge

6. 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

7. 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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Stepne Manor

8. 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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Thornton Estate

9. 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.