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Chestertown Rentals

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Price range

Per night

$10 - $500

Chestertown Rentals

21 Houses

Cottage On Kent

Chestertown cottage

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$196

1 / 7

Cozy & Spacious Chestertown Home

Chestertown house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 2 minutes

Price per night from

$251

1 / 28

Chester River House with Views

Chestertown house

3 bedrooms / 1 bathroom / sleeps 7

Responds fast! avg. 1 hour 40 minutes

Price per night from

$155

1 / 11

Belle Rose Cottage at Victory Farm (Pet Friendly!)

Chestertown house

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$136

1 / 17

Gorgeous Home on Chester River

Chestertown house

4 bedrooms / 9 bathrooms / sleeps 8

Price per night from

$651

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

Price per night from

$295

1 / 14

Sunview Cottage on Chesapeake Bay

Chestertown house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 2 hours 19 minutes

Price per night from

$145

1 / 22

Cozy Apartment in Chestertown

Chestertown apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 19 minutes

Price per night from

$88

1 / 7

Charming Apartment in Historic Chestertown, MD

Chestertown apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 19 minutes

Price per night from

$99

1 / 10
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