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Chestertown Rentals

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Price range

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$10 - $500

Chestertown Rentals

21 apartments

Charming Apartment in Historic Chestertown, MD

Chestertown apartment

1 bedroom / 1 bathroom / Sleeps 2

Responds fast! avg. 3 hours 2 minutes

$99

1 / 10

Belle Rose Cottage at Victory Farm (Pet Friendly!)

Chestertown house

1 bedroom / 1 bathroom / Sleeps 3

$136

1 / 17

Gorgeous Home on Chester River

Chestertown house

4 bedrooms / 9 bathrooms / Sleeps 8

$651

1 / 16

Sunview Cottage on Chesapeake Bay

Chestertown house

2 bedrooms / 1 bathroom / Sleeps 5

Responds fast! avg. 3 hours 2 minutes

$115

1 / 22

Cozy Apartment in Chestertown

Chestertown apartment

1 bedroom / 1 bathroom / Sleeps 2

Responds fast! avg. 3 hours 2 minutes

$88

1 / 7

Chester River House with Views

Chestertown house

3 bedrooms / 1 bathroom / Sleeps 7

Responds fast! avg. 3 hours 4 minutes

$155

1 / 11

Retreat at a quiet, water front cottage

Chestertown house

3 bedrooms / 3 bathrooms / Sleeps 8

“A best kept secret!” I have had the pleasure of staying at Cliff Point many times. The view cannot be matched, water views more than 180 degrees, sunsets are stunning. But on top of that the house is so comfortable and charming, spacious and cozy. Ch

$296

1 / 14

Cozy & Spacious Chestertown Home

Chestertown house

4 bedrooms / 3 bathrooms / Sleeps 8

Responds fast! avg. 1 hour 56 minutes

$200

1 / 25
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