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Chestertown Rentals

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Price range

Per night

$10 - $500

Chestertown Rentals

8 apartments

Gorgeous Home on Chester River

Chestertown house

4 bedrooms / 9 bathrooms / Sleeps 8

$655

1 / 16

Chester River House with Views

Chestertown house

3 bedrooms / 1 bathroom / Sleeps 7

$157

1 / 11

Retreat at a quiet, water front cottage

Chestertown house

3 bedrooms / 3 bathrooms / Sleeps 8

“Blissful, Expansive water views with awesome sunsets!” This rental has everything you could possibly need. A public boat launch a 1/4 mile or less from the house. Kayaks and a large amount of water to explore. A gorgeous 10 mile drive or bike ride fro

$295

1 / 14

Charming Apartment in Historic Chestertown, MD

Chestertown apartment

1 bedroom / 1 bathroom / Sleeps 2

$89

1 / 10

Sunview Cottage on Chesapeake Bay

Chestertown house

2 bedrooms / 1 bathroom / Sleeps 5

$115

1 / 22

Cozy Apartment in Chestertown

Chestertown apartment

1 bedroom / 1 bathroom / Sleeps 2

$89

1 / 7

Belle Rose Cottage at Victory Farm (Pet Friendly!)

Chestertown house

1 bedroom / 1 bathroom / Sleeps 3

$136

1 / 17

Cozy & Spacious Chestertown Home

Chestertown house

4 bedrooms / 3 bathrooms / Sleeps 8

$202

1 / 25
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