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Chestertown Rentals

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Price range

Per night

$10 - $500

Chestertown Rentals

21 apartments

Cozy & Spacious Chestertown Home

Chestertown house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 19 minutes

$250

1 / 28

Chester River House with Views

Chestertown house

3 bedrooms / 1 bathroom / sleeps 7

Responds fast! avg. 2 hours 30 minutes

$155

1 / 11

Sunview Cottage on Chesapeake Bay

Chestertown house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 3 hours 8 minutes

$115

1 / 22

Charming Apartment in Historic Chestertown, MD

Chestertown apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 8 minutes

$99

1 / 10

Belle Rose Cottage at Victory Farm (Pet Friendly!)

Chestertown house

1 bedroom / 1 bathroom / sleeps 3

$134

1 / 17

Gorgeous Home on Chester River

Chestertown house

4 bedrooms / 9 bathrooms / sleeps 8

$650

1 / 16

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

$295

1 / 14

Cozy Apartment in Chestertown

Chestertown apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 8 minutes

$88

1 / 7
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