Performance indicators for the Woodstock short-term rental market based on reliable data.
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The highest-performing listings in Woodstock.
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Challenging to Investors
STRs are explicitly legal but subject to strict caps and special permits for most categories; non-owner-occupied units face a hard 180-day cap (and a 26‑weekend limit) and require a county registration, annual inspections, safety/parking plans, and moderate fees, which together dampen investor viability.
Local STR Agent
STR specialist · Woodstock, NY
Woodstock, NY, is a small yet vibrant town located in the Catskill Mountains in Ulster County. It has a population of approximately 6,000 residents. The town is about 110 miles (177 kilometers) north of New York City, making it a popular getaway destination for urban dwellers seeking a retreat into nature.
Woodstock is renowned for its rich artistic heritage and cultural significance. A key landmark is the Woodstock Playhouse, a historic venue that stages a variety of live performances and has roots in the 1900s. In addition, the town has a distinct charm characterized by its eclectic shops, galleries, and restaurants lining Tinker Street.
For nature enthusiasts, the Overlook Mountain trail provides breathtaking views of the Hudson Valley and is a favorite spot for hiking. The property near the mountain also includes the ruins of the historic Overlook Mountain House—a former luxurious hotel.
Moreover, Woodstock's proximity to renowned locations like the Woodstock Artists Association & Museum (WAAM) ensures that visitors have ample opportunity to engage with the local art scene, which has thrived since the early 20th century.
Given this blend of cultural richness and natural beauty, Woodstock offers an appealing environment for short-term rentals. It attracts a diverse array of visitors looking to experience its artistic atmosphere and outdoor adventures, whether they are attending a performance or exploring the scenic landscapes.