Skip to content
ASTRO
Continue with email

Maryland

Chestertown, Maryland

17 rentals4 hotels5 things to doRegulated owner rules
Chestertown, Maryland city hub image

Own one of these properties? Claim it →

Chestertown is an incorporated city in Maryland. ASTRO catalogs short-term rentals here for travelers seeking a base in this locality.

STAY

Independent vacation rentals in Chestertown

17 independent vacation rentals on file

Browse places in Chestertown →

HOTELS

Hotels & motels in Chestertown

4 hotels & motels on file

THINGS TO DO

Things to do in Chestertown

City Watch · for owners

How Chestertown controls vacation rentals

Regulated · moderate intensityRegistrationPermitOwner-occupiedTaxedas of Sep 15, 2026
See the rules for Chestertown

Own one of these properties in Chestertown?

These are public registry records in the ASTRO Network — identity and discovery, not a booking checkout. Owners claim and verify their place to add photos, links, and details and to earn the green Verified mark.

Be the first verified owner in Chestertown.

NEARBY

Nearby destinations

Rock Hall — 10 miBetterton — 11 miQueenstown — 18 miAberdeen — 22 miBel Air — 23 miHavre de Grace — 24 miChesapeake City — 25 miNorth East — 26 miChestertown
Chestertown and nearby cities. Tap a star to explore that destination.

PROS

Professionals for STR owners

Property managers, photographers, lenders and other services for short-term rental owners. Browse the ASTRO pros directory →

Home › Maryland › Chestertown › Properties