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Olivebridge, NY
Challenging To Investors
Local STR Agent
Local STR Agent

Short-term rentals are allowed in Olivebridge, NY, but with significant restrictions under Town of Olive Local Law No. 2 of 2022. The town has implemented comprehensive regulations to balance the economic benefits of STRs with the preservation of long-term housing stock. Olivebridge, located within the Town of Olive in Ulster County, operates under a permit-based system with strict caps on the number of allowable STRs, mandatory safety inspections, and specific owner-occupancy requirements that heavily favor full-time residents.
Olivebridge hosts earn a median $42,720/year with $267 ADR and 56% occupancy.
Top performers pull in $57,389+ per year.
See the full Olivebridge market breakdownTown of Olive STR Permit
Ulster County Hotel & Motel Occupancy Tax Registration
Required Safety Equipment:
Inspection Requirements:
Property Documentation:
Owner/Host Documentation:
Residency Verification:
Rental Duration and Occupancy:
Property Restrictions:
Address and Identification:
Annual Operation Limits:
Hotel & Motel Occupancy Tax:
Building and Fire Safety:
Water and Wastewater:
All STR units must post comprehensive House Rules including:
Town of Olive Building Department
Code Enforcement Officer
Ulster County Commissioner of Finance
Primary Regulatory Documents:
Official Town Resources:
Additional Resources:
Current Application Status: As of January 2023, the Town of Olive was reported as "Currently NOT accepting new applications," suggesting potential caps may have been reached or temporary moratoriums in effect.
Environmental Considerations: The Town of Olive operates within the New York City watershed, making water and wastewater management particularly sensitive. Annual water testing and careful occupancy management are critical.
Market Reality: The regulations are specifically designed to favor owner-occupied STRs and limit investment property conversions, reflecting the town's priority on preserving long-term rental housing stock for full-time residents.
Compliance Costs: Beyond permit fees, investors should budget for annual safety inspections, water testing, and potential septic system maintenance or upgrades to meet regulatory standards.
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Revenue data, top neighborhoods, seasonal trends, and the key regulations for Olivebridge, New York in one email.

Olivebridge is a small hamlet in the town of Olive in Ulster County, New York, tucked into the wooded foothills of the Catskill Mountains. With a population of just a few hundred residents, the community has the quiet, rural character that defines much of the central Catskills, and it serves as a natural gateway to the Ashokan Reservoir, the surrounding Catskill Park, and the broader Ulster County recreation region. The hamlet sits roughly 15 to 20 miles west of Kingston — the county seat and nearest city — and approximately two to two-and-a-half hours north of New York City, making it reachable for weekend escapes from the metropolitan area.
Just minutes from the center of Olivebridge lies the Ashokan Reservoir, one of New York City's largest upstate water supplies and a defining feature of the surrounding landscape. A gravel walking and cycling path follows a long stretch of the reservoir's southern shore, drawing visitors for its broad views of the water, the forested ridges beyond, and the historic bridge that connects the reservoir's two basins. The area is popular year-round and especially striking in autumn, when the surrounding hardwood slopes turn color.
About 20 to 25 minutes south of Olivebridge, Minnewaska State Park Preserve sits atop the Shawangunk Ridge and offers a markedly different landscape of sky lakes, sandstone cliffs, and pitch-pine barrens. The preserve is laced with carriage roads and footpaths that lead to waterfalls, cliff-edge viewpoints, and cool swimming holes, and it draws hikers, rock climbers, mountain bikers, and cross-country skiers across the seasons. Its elevation affords long westward views across the Rondout Valley and toward the higher Catskill peaks.
A short drive northwest of Olivebridge brings visitors to Phoenicia, a small Catskills hamlet long associated with the railroad and the river that runs through it. Esopus Creek, which winds through the village, is a regional draw for tubing, kayaking, and fly-fishing in the warmer months, and the compact main street holds a handful of restaurants, outfitters, and small shops. Phoenicia also serves as a staging point for hikes into the nearby Slide Mountain Wilderness and other corners of the central Catskill backcountry.
Olivebridge's appeal as a short-term rental base comes from the way it pairs a quiet, tree-shaded setting with quick access to the region's marquee outdoor destinations. Guests can spend their mornings on reservoir paths, afternoons on ridge-top trails, and evenings in nearby small towns, all while staying within an easy drive of Kingston, Woodstock, and the broader Ulster County road network. For owners, that combination of seclusion, scenery, and proximity to multiple Catskills draws makes the hamlet a natural fit for travelers seeking an outdoor-focused upstate stay.
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