Some Dutchess towns cap un-hosted STR rentals at a set number of nights per year. Town of Rhinebeck limits un-hosted short-term rentals to approximately 60-90 nights per year; hosted rentals (owner on-site) face no annual night cap. Town of Red Hook and Town of Milan have similar tiered frameworks.
Un-hosted (whole-house) STRs are regulated more tightly than hosted rentals across Dutchess County. Town of Rhinebeck Chapter 125 caps un-hosted STRs at 60-90 rental nights per calendar year with permit conditions tracked via a booking log. Town of Red Hook Chapter 143 uses a similar tiered cap. Hosted STRs (owner/principal resident on-site during rental) typically face no night cap but must comply with occupancy and parking rules. Dutchess County has no countywide night cap; rural agricultural towns (Milan, Stanford, Pine Plains, Amenia) often impose no cap. Under NY's December 2024 statewide STR framework, platforms must report quarterly to NYS Tax and Finance starting March 25, 2025, enabling enforcement of town-level night caps. Violations typically trigger $500 per night over cap plus permit revocation for repeat offenders.
Over-cap rental: $500 per night over limit in Rhinebeck and Red Hook. Repeat violation: permit revocation and 1-3 year re-application prohibition. Failure to log bookings: $250-$500 per audit failure. Platform non-reporting under 2024 law: NYS Tax enforcement.
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