City Watch
Short-term rental rules in Chestertown, MD
How Chestertown regulates short-term rentals: the rules that apply, their sources, and pending changes.
Short-term rentals here operate under a registration or permit system with ongoing operating rules.
- town STR-specific registration + license process in force (Town Code Chapter 138)
- whole-home / non-owner-occupied STRs are the express subject of the registration regime — absentee permitted, not foreclosed
- no cap, quota, primary-residence, or host-present requirement found
- layered county STR tax + MD state STR Commission registration on top
Based on: Chestertown Town Code Chapter 138 — Registration of Non-Owner-Occupied Short-Term Rental Units (adoption date/ordinance
Summary of the rule
Chapter 138: Registration of Non-Owner-Occupied Short-Term Rental Units
View the ordinance source ↗✓ Verified
Last reviewed Sep 15, 2026 · Sources · Report an error
Pending legislation
Monitoring Chestertown · system last checked Oct 25, 2026
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City Watch tracks changes from public sources — council agendas, state bills, local news — not a complete legal compendium.
A city permit is not the whole picture — HOA, condominium, deed, or lease rules may be stricter.
City Watch provides good-faith summaries of publicly available information as of the review date shown. Rules, enforcement, and permit availability can change, and summaries may contain errors or omissions. Ratings describe the general regulatory environment; they do not establish whether a particular property or stay is permitted. This is general information, not legal advice. Before buying, listing, or hosting, verify applicable requirements with the responsible authorities and review any HOA, condominium, deed, or lease restrictions.