Windham, NY

Windham is a small mountain town in Greene County, New York, nestled in the northern reaches of the Catskill Mountains. With a population of roughly 1,600 residents, the community has the quiet, wooded character of an upstate retreat while serving as a year-round hub for outdoor recreation. It is best known as a gateway to high-elevation skiing and the surrounding Northern Catskills, and it sits approximately 130 miles north of New York City — about a two-and-a-half-hour drive via the New York State Thruway — and roughly 50 miles south of Albany.

Windham Mountain is the town's signature draw, a four-season resort that has anchored the local economy for decades. In winter the mountain offers skiing and snowboarding terrain, and in warmer months it converts to a destination for downhill mountain biking, an alpine coaster, and scenic chairlift rides. The resort is just a few minutes from the center of town.

Just down the road, Hunter Mountain in the adjacent town of Hunter expands the ski options and adds a full events calendar that has historically drawn large crowds to the region in both winter and summer. The drive between the two resorts is only about ten minutes, allowing visitors to base in Windham and easily sample both mountains in a single trip.

The surrounding Catskill Park, a vast network of public and private lands covering more than 700,000 acres, offers endless opportunities for hiking, leaf-peeping, and exploring. A standout within the park is Kaaterskill Falls, one of the tallest two-stage waterfalls in the eastern United States, with a trailhead roughly twenty minutes from Windham that draws photographers and hikers throughout the year.

For those interested in the region's cultural roots, the Thomas Cole National Historic Site in Catskill — about 45 minutes south — preserves the home and studios of the painter widely regarded as the founder of the Hudson River School. The site offers tours that connect the very mountain landscapes around Windham to the birth of American landscape painting.

Windham's combination of small-town atmosphere, a marquee ski resort, immediate access to the broader Catskill Park, and proximity to both New York City and Albany makes it a versatile base for short-term rentals. Guests come for winter powder and summer trails, but they return for the slower pace, the mountain views, and the sense that a real upstate community — not just a resort — is waiting at the end of the road.