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Woodstock, NY
Challenging To Investors
Local STR Agent

Yes, short-term rentals are explicitly allowed in Woodstock, NY under specific regulatory framework established by Local Law No. 1 of 2019. The Town of Woodstock permits and regulates STRs as accessory uses or supplementary businesses, with distinct categories for different property types and occupancy scenarios. However, the regulations are structured to balance tourism benefits with housing protection, implementing caps on the number of permitted STRs and imposing specific operational requirements that vary based on ownership and property characteristics.
Before purchasing or converting any property for STR use, conduct thorough due diligence to verify:
Woodstock's regulations classify STRs into three distinct categories, each with different requirements and operational limitations:
A. Short-Term Rental Home (STR Home)
B. Short-Term Rental Establishment
C. Non-Owner Occupied Short-Term Rental
Annual Operating Permit (Primary Requirement)
Ulster County Registration
Completed Annual Permit Application
Safety/Egress Plan
Parking Layout Plan
Garbage Removal Plan
Host Designation (Non-Owner Occupied STRs Only)
Occupancy Documentation
Ulster County Registration Copy
Annual Fire/Safety Inspection Report
Registration Number Display
Guest Information Package
Town Board Authority: The Town Board annually sets caps on both owner-occupied and non-owner occupied STRs permitted within town limits, along with corresponding fee schedules.
Individual Property Owner Limits:
Parking Standards:
Safety and Egress:
Sales Tax Requirements:
Hotel Occupancy Tax:
Violation Consequences:
Woodstock Building Department
Town Supervisor
As of January 2025, Woodstock implemented a new fee structure designed to support full-time residents:
Current Fee Schedule:
The town is also monitoring state-level legislation requiring STR owners to register with New York State, which would provide municipalities with detailed monthly reports on rental activities and enable tax collection.
Important Note: In August 2023, Woodstock temporarily suspended STR permit applications for six months. While applications appear to have resumed, investors should confirm current application status with the Building Department before proceeding with any property acquisitions or conversions.




Woodstock, NY, is a small yet vibrant town located in the Catskill Mountains in Ulster County. It has a population of approximately 6,000 residents. The town is about 110 miles (177 kilometers) north of New York City, making it a popular getaway destination for urban dwellers seeking a retreat into nature.
Woodstock is renowned for its rich artistic heritage and cultural significance. A key landmark is the Woodstock Playhouse, a historic venue that stages a variety of live performances and has roots in the 1900s. In addition, the town has a distinct charm characterized by its eclectic shops, galleries, and restaurants lining Tinker Street.
For nature enthusiasts, the Overlook Mountain trail provides breathtaking views of the Hudson Valley and is a favorite spot for hiking. The property near the mountain also includes the ruins of the historic Overlook Mountain House—a former luxurious hotel.
Moreover, Woodstock's proximity to renowned locations like the Woodstock Artists Association & Museum (WAAM) ensures that visitors have ample opportunity to engage with the local art scene, which has thrived since the early 20th century.
Given this blend of cultural richness and natural beauty, Woodstock offers an appealing environment for short-term rentals. It attracts a diverse array of visitors looking to experience its artistic atmosphere and outdoor adventures, whether they are attending a performance or exploring the scenic landscapes.
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