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Find places to stay in Chestertown

Vacation rentals from professional hosts. Book direct, skip the platform markup.

Chestertown Vacation Rentals

Chestertown Vacation Rentals

Find places to stay in Chestertown

Vacation rentals from professional hosts. Book direct, skip the platform markup.

Stop overpaying for
vacation rentals.

Trending stays in Chestertown

7% savings

Pet-Friendly Home on Chester River w/ Dock!

House in Chestertown, MD

Hosted by Evolve

Feb 16 – Feb 21

7% savings

Pet-Friendly Home on Chester River w/ Dock!

House in Chestertown, MD

Hosted by Evolve

Feb 16 – Feb 21

15% savings

Harbor View Haven

House in Chestertown, MD

Hosted by BNB BREEZE

Feb 22 – Feb 27

15% savings

Harbor View Haven

House in Chestertown, MD

Hosted by BNB BREEZE

Feb 22 – Feb 27

16% savings

Langford Creek Estate

House in Chestertown, MD

Hosted by BNB BREEZE

Feb 11 – Feb 16

16% savings

Langford Creek Estate

House in Chestertown, MD

Hosted by BNB BREEZE

Feb 11 – Feb 16

1% savings

Walk to Historic Chestertown: Dog-Friendly Retreat

House in Chestertown, MD

Hosted by Evolve

Mar 2 – Mar 7

1% savings

Walk to Historic Chestertown: Dog-Friendly Retreat

House in Chestertown, MD

Hosted by Evolve

Mar 2 – Mar 7

15% savings

3 Mi to Washington College! Updated Home w/ Patio

House in Chestertown, MD

Hosted by Evolve

Feb 13 – Feb 18

15% savings

3 Mi to Washington College! Updated Home w/ Patio

House in Chestertown, MD

Hosted by Evolve

Feb 13 – Feb 18

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Nearby Cities

Ocean City, MD, USA