Short-term rental permit rules in Middletown, NY — also called Airbnb permits, vacation rental licenses, or STR registration — list the application steps, fees, and operating requirements for hosting.
Orange County NY has no countywide STR registration. Warwick, Highland Falls, and Woodbury regulate locally. Since March 25, 2025, NY State requires Airbnb/VRBO to collect 4 percent state sales tax plus local taxes and report quarterly under the Hochul STR law.
Orange County has not created a countywide STR registry, but New York State enacted its first statewide STR framework in December 2024 (signed by Gov. Hochul). Effective March 25, 2025, platforms like Airbnb and VRBO must collect and remit 4 percent NY state sales tax plus local taxes on all stays under 30 days and file quarterly reports. Counties may opt in to a county-wide registry. At the municipal level: Town of Warwick requires a STR permit with annual inspection and a $300 fee. Village of Highland Falls (near West Point) requires registration and a $150 annual fee. Town of Woodbury (home to Woodbury Common Premium Outlets) requires site-plan review for new STRs. City of Newburgh and City of Middletown have no specific STR law yet but enforce zoning residential-use definitions. Owner-occupied 2-unit STRs are often treated as boarding houses.
Operating STR without Warwick permit: $250-$1,000 per night; repeat violations lead to permit denial. Unregistered STR in Highland Falls: up to $500 plus cease-and-desist.
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