Hotels in Chestertown (Maryland, USA)

115 hotels in Chestertown

  1. Comfort Inn & Suites Chestertown

    Seasonal outdoor swimming pool
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  2. Red Roof Inn & Suites Chestertown

    Historic Chestertown waterfront access
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  3. The Lodge at Great Oak Landing

    Marina views and activities
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  4. Brampton 1860

    In-room spa services
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  5. Driftwood Inn

    Seasonal outdoor swimming pool
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  6. Walk to Historic Chestertown: Dog-Friendly Retreat

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  7. Rubys Sea Glass Cottage

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  8. Water Front Retreat - Sunrise And Sunset Water Views - Lots Of Amenities

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  9. Historic Downtown Garden Oasis With Private Patio

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  10. Comfort Suites

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  11. Great Oak Manor

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  12. Cozy Victorian Downtown Home

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  13. Anchors Away!

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  14. Cozy 5 Bedroom House W/ Attached Guest Suite In Worton, Md

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  15. Porterhouse Farm

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  16. Pet-Friendly Home on Chester River w/ Dock!

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  17. Chesapeake Getaway - Marinas - Woodland Views

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  18. Riverside at Pear Tree Point--Waterfront Escape

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  19. Cozy 1-bedroom house in lovely Chestertown with AC

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  20. Welcome to the magic of Langford Creek Farm

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  21. Eastern Shore Maryland 2 Minute Walk To Beach; Quintessential Beach Home

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  22. Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown

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  23. Brand New Cottage Steps From The Beach!

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  24. Waterfront House, - Pier, Close To Betterton - Chestertown & Rockhall

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  25. Chester River Waterfront, Magnificent Views, Dock, Beach

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  26. Stunning Historic Downtown Home!! Within 2 Blocks Of Fountain Park!!

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  27. Private Waterfront Cottage On Langford Creek With Hot Tub & Pier

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  28. Guest Lodge | Private Pool | Outdoor Dining | Game Room

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  29. Relaxing House In The Heart Of Downtown - Walking Distance To Everything

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  30. Waterfront Millington Vacation Rental W/ Hot Tub!

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  31. Blue Heron Farm Waterfront Chalet

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  32. A Waterfront Oasis With Pier And Pool. Spacious 4 Bedrooms Near Chestertown.

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  33. Bay Cliff: Vacation On The Eastern Shore

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  34. Waterfront Home W/ Private Dock & Hot Tub - Harbor View Haven

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  35. Manor House On Beautiful Eastern Shore Estate

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The prices and availability we receive from booking sites change constantly. This means you may not always find the exact same offer you saw on trivago when you land on the booking site.

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