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Vacation Rentals in Chestertown

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4BR waterfront home outside Chestertown, wide water views! – Property 7004812

  • Chestertown rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, DVD, fireplace
  • $1,253 - $1,976/week
  • Calendar Last Updated On: Nov 21, 2009
The ever-changing Chester River is the focal point of the house. Watermen called this section of the river “Moon Bay," hence the name The River House on Moon Bay.

Chesapeake Bay, Water Front, Private Home & Dock, 3.5 Acres – Property 211184

  • Chestertown rental - house, 4 bedrooms, sleeps 10, 3 bathrooms, rural, waterfront, pets considered
  • Calendar Last Updated On: Nov 15, 2009
Enjoy the Eastern Shore's quiet and relaxed atmosphere. If you've never been to the Eastern Shore, you're in for a treat. If you are a veteran of Chesapeake Bay,...

Cozy up by the Big Stone Fireplace For the Holidays and Enjoy the Waterviews – Property 254204

  • Chestertown rental - house, 6 bedrooms, sleeps 12, 6 bathrooms, rural, waterfront, garden
  • $2,695 - $5,495/week
  • Calendar Last Updated On: Nov 12, 2009
Expansive views with 3/4 of an acre of water frontage. Very private and serene, great for birdwatching, geese migration, kayaking and boating.
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