Are you in a hurry?
Here is a quick list of Vacation Rentals in Chestertown, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| Home Away |
9.7 / 10 (72 Reviews) |
From 76$ | |
| On Ensor |
8.9 / 10 (226 Reviews) |
From 80$ | |
| Whispering Oak Mansion |
8.9 / 10 (153 Reviews) |
From 157$ | |
| Stylist Bedroom Central Of Baltimore |
7.8 / 10 (406 Reviews) |
From 62$ | |
| Gaia House |
9.0 / 10 (57 Reviews) |
From 137$ |
Chestertown offers a rich blend of charming architecture and picturesque scenery, making it an ideal location for vacation rentals. Whether you are seeking a cozy cottage along the waterfront or a spacious home in the heart of the town, you will find a variety of options to suit your needs. From unique historical homes to modern accommodations, Chestertown provides choices for every type of traveler. This town is perfect for families, couples, and groups looking to create unforgettable memories. With numerous outdoor activities and local attractions nearby, Chestertown is the perfect destination for your next getaway.
Best Chestertown Vacation Rentals
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3 Mi To Washington College! Updated Home W/ Patio
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Pet-Friendly Home On Chester River W/ Dock!
From 793$
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Walk To Historic Chestertown: Dog-Friendly Retreat
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Home Away
From 76$
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On Ensor
From 80$
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Whispering Oak Mansion
From 157$
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Stylist Bedroom Central Of Baltimore
From 62$
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Gaia House
From 137$
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Cozy Room In Baltimore City
From 58$
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Watch Deer From A Farm Cottage
From 262$
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House On The Gwynns Falls
From 194$
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King Suite And Sofa Bed Fast Wi-Fi Easy Dc Access
From 77$
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Baltimore Abode, Walk To Cross Street Market!
From 400$
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Exquisite & Serene 1 Bedroom, 1 Full Bath Apartment
From 164$
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Private Studio Apartment With One King Bed And One Sofa Bed
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Lg Cozy Room, Shared Bathroom
From 73$