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Hillsdale, NY
Very Investor Friendly
Local STR Agent
Local STR Agent

YES, short-term rentals are explicitly allowed in Hillsdale, NY. The Town has adopted comprehensive regulations for "Transient Rentals" (defined as rentals fewer than 30 days), specifically including online platform bookings such as Airbnb and HomeAway. Hillsdale's framework provides a clear pathway for STR operations through a permit and inspection system designed to ensure safety and neighborhood compatibility.
Hillsdale hosts earn a median $33,551/year with $304 ADR and 44% occupancy.
Top performers pull in $51,427+ per year.
See the full Hillsdale market breakdown →Initial Assessment
Columbia County Registration (First)
Zoning Board of Appeals (ZBA) Application
Building Department Application
Inspection Process
Operational Setup
Special Permit ($50)
Certificate of Occupancy/Compliance ($150)
Local Contact Designation
Columbia County Registration
Occupancy Tax Compliance
NYS Sales Tax
NYS Uniform Code Compliance
Town of Hillsdale Code Enforcement Officer
Columbia County Treasurer's Office
Town Board/Clerk:
This regulatory framework provides clear guidelines for operating compliant short-term rentals in Hillsdale while ensuring community standards and safety requirements are met.
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Hillsdale is a town in Columbia County, New York, near Hudson, New York and Great Barrington, Massachusetts. State routes 22 and 23 intersect near the town center, which is listed on the National Register of Historic Places. The town has several restaurants and a general store, among other businesses. Hillsdale is known for its hilly landscape and is near Bash Bish Falls, Taconic State Park, and the Catamount Ski Area. The Harlem Valley Rail Trail, a 26-mile bike path in two sections, is located not far from the intersection of routes 22 and 23.
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