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Generally Investor friendly
STRs are allowed with no caps and low regulation, but require county registration, safety inspections, and annual renewals plus standard state/local taxes and sales tax compliance; the town’s draft regulations under review create uncertainty for future restrictions.
Local STR Agent
STR specialist · Roxbury, NY
Roxbury is a small rural town in Delaware County, New York, tucked into the northern reaches of the Catskill Mountains. With a population of roughly 2,400, the town has the quiet, unhurried character that defines the so-called "forever wild" Catskill region. It is best known as a base for outdoor recreation and as one of the oldest settled communities in the Catskills, with a Historic District on Main Street and connections to nineteenth-century Hudson River School painters. Roxbury lies about 130 miles northwest of New York City, an approximate three-hour drive via the New York State Thruway and State Route 30, making it far enough to feel like a genuine escape yet close enough for a long weekend.
The dominant draw for visitors is the surrounding Catskill Park, a vast preserve of forested mountains, trout streams, and hiking trails. From Roxbury, trailheads for peaks in the central Catskills are within a half-hour drive, offering everything from short family walks to more serious climbs with sweeping valley views. The town is also within easy reach of the Pepacton Reservoir, a large impoundment of the East Branch of the Delaware River, where shoreline access points offer fishing and paddling during the warmer months.
A short fifteen-minute drive to the south brings visitors to the village of Margaretville, the commercial hub of the surrounding mountains, with small restaurants, antique shops, and a year-round community feel that gives the area its slow-paced identity. To the west lies the town of Andes, another Catskills village known for its Main Street, art galleries, and live music scene; both neighboring villages make popular day trips for guests staying in Roxbury. Together with the surrounding hamlets of Grand Gorge, Halcottsville, and Denver, they form the kind of interconnected rural network that encourages slow exploring rather than checklist tourism.
In winter, Roxbury is within roughly thirty to forty-five minutes of several small ski areas, including Plattekill Mountain and Belleayre Mountain, both family-oriented operations that draw regional skiers without the scale or crowds of larger resorts. Spring through fall, the same region offers tubing on the East Branch, swimming holes, and leaf-peeping routes that loop back through Roxbury's covered bridges and historic farmsteads. As an alternative to the more developed Catskills towns to the south, Roxbury appeals to travelers who want a quieter base with the same mountain scenery and easy access to the wider Catskill region.
Roxbury makes a compelling base for short-term rentals precisely because it offers the calm of a small mountain town while keeping a wide range of Catskill experiences within easy reach. Guests can spend a morning on a wooded trail, an afternoon browsing a neighboring village, and an evening back at a quiet rental — all without the traffic and density of the more heavily marketed Catskill towns. For owners, that combination of authenticity, scenery, and proximity to New York City supports steady interest from outdoor-oriented and second-home travelers year-round.