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Brampton 1860

1. 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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Great Oak Manor

2. Great Oak Manor

 Chestertown, Maryland
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Inn at Mitchell House

3. Inn at Mitchell House

 Chestertown, Maryland
Beauty undisturbed. Historic manor offers a tranquil retreat. Approximately 10 miles outside of Chestertown.
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Rolph's Wharf, The River Inn

4. 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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Thornton Estate

5. 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

6. White Swan Tavern

 Chestertown, Maryland