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Montgomery, NY
Generally Investor Friendly
Local STR Agent
Local STR Agent

Yes—short-term rentals (STRs) are permitted in the Town of Montgomery, New York (Orange County), but only under a formal, revocable permit regime with strict eligibility, safety, and operational standards. The key constraints are:
Operators must meet rigorous safety and code requirements, maintain insurance, adhere to occupancy limits, and post required notices and documents on-site. Violations can trigger fines, permit suspension, or revocation.
Note: The provided sources also contain extensive materials for Montgomery County, Maryland—this guide focuses strictly on Montgomery, New York (Orange County), and cites only the NY-specific ordinance.
Montgomery hosts earn a median $46,571/year with $194 ADR and 60% occupancy.
Top performers pull in $58,564+ per year.
See the full Montgomery market breakdownStep 1: Confirm Eligibility
Step 2: Prepare Application Package
Step 3: Submit Application and Fees
Step 4: Neighbor Notification and Review
Step 5: Inspection and Approval
Step 6: Post-Permit Setup
Step 7: Ongoing Operations and Renewal
Pre-existing STRs: If the property was actively operated as an STR for at least one calendar year prior to the effective date of the law, you may apply to continue the use, subject to standards and documentation within 60 days of the effective date; the law also includes specific continuity protections and restrictions on expansion for such pre-existing STRs.
Short-Term Rental Permit (Revocable; 2-year term; non-transferable)
Application Requirements (submitted to Building Department)
Insurance
Property Documentation (for septic/water)
Operational Documentation
Signage
Fees
Eligibility and Use
Property Standards
Occupancy Limits
Safety and Utilities
Rental Contract and Good Neighbor Standards
Process and Inspections
Display Requirements
Existing Short-Term Rentals
Compliance, Penalties, and Enforcement
Permit Renewal
Grounds for Immediate Suspension or Revocation
Appeals
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Montgomery is a town in Orange County, New York, situated in the lower Hudson Valley roughly sixty miles north of New York City. With a population of approximately twenty-three thousand, the town encompasses a historic village core surrounded by rolling farmland, orchards, and the wooded slopes of the surrounding ridges. It serves as a convenient base for travelers exploring the Hudson Valley's wineries, outdoor recreation, and cultural landmarks, and is often used as a gateway to the Shawangunk Ridge and the broader Orange County region.
Just outside Montgomery, in the neighboring town of Washingtonville, Brotherhood Winery claims the title of America's oldest operating winery, with roots reaching back to 1839. Visitors can tour the historic underground cellars, sample vintages in the tasting room, and explore the manicured grounds, all within roughly ten minutes of the village center.
A short drive south brings travelers to Storm King Art Center, a sprawling five-hundred-acre outdoor sculpture park set against the dramatic backdrop of Storm King Mountain in the Hudson Highlands. About twenty-five minutes from Montgomery, the center features monumental works by artists such as Alexander Calder, Mark di Suvero, and Maya Lin, and is widely regarded as one of the premier sculpture parks in the country.
Shoppers will find the renowned Woodbury Common Premium Outlets in Central Valley, roughly ten to fifteen minutes from Montgomery. With hundreds of stores spread across a vast open-air campus, the outlet center draws visitors from across the New York metropolitan area and beyond, making it one of the most-visited retail destinations in the region.
For outdoor enthusiasts, the Shawangunk Ridge and Minnewaska State Park Preserve lie about thirty to forty minutes west of Montgomery. The ridge is renowned among rock climbers for its white conglomerate cliffs, while the park preserve offers miles of carriage roads, sky lakes, waterfalls, and sweeping views of the Catskills and Hudson Valley — a draw in every season.
With its central position in Orange County, its proximity to the New York metropolitan area, and its easy access to wineries, cultural landmarks, outlet shopping, and some of the Northeast's most celebrated outdoor landscapes, Montgomery offers a versatile foundation for short-term rental guests. The town's blend of small-village character and regional connectivity makes it well suited to travelers seeking a quieter Hudson Valley home base without sacrificing convenience to the area's marquee destinations.
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