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Chestertown Rentals

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Price range

Per night

$10 - $500

Chestertown Rentals

21 Houses

Cozy & Spacious Chestertown Home

Chestertown house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 10 minutes

1 / 28

Chester River House with Views

Chestertown house

3 bedrooms / 1 bathroom / sleeps 7

Responds fast! avg. 2 hours 6 minutes

1 / 11

Gorgeous Home on Chester River

Chestertown house

4 bedrooms / 9 bathrooms / sleeps 8

1 / 16

Belle Rose Cottage at Victory Farm (Pet Friendly!)

Chestertown house

1 bedroom / 1 bathroom / sleeps 3

1 / 17

Cottage On Kent

Chestertown cottage

1 bedroom / 1 bathroom / sleeps 3

1 / 7

Cozy Apartment in Chestertown

Chestertown apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 19 minutes

1 / 7

Charming Apartment in Historic Chestertown, MD

Chestertown apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 19 minutes

1 / 10

Retreat at a quiet, water front cottage

Chestertown house

3 bedrooms / 3 bathrooms / sleeps 8

1 / 14

Sunview Cottage on Chesapeake Bay

Chestertown house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 2 hours 19 minutes

1 / 22
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