Short Term Rental Investment Properties for Sale in Poughkeepsie, NY

Poughkeepsie offers a moderately regulated short-term rental market with relatively lenient enforcement compared to neighboring Hudson Valley towns, making it accessible for new STR investors. The city's complaint-driven enforcement model allows compliant hosts to operate with minimal interference, while strong seasonal demand—particularly during summer and fall tourism peaks—supports consistent occupancy rates. With primary residence requirements and permit caps (30 unhosted commercial permits annually), the market remains competitive but not oversaturated. The emerging regulatory framework, including potential additional hotel occupancy taxes up to 9%, requires careful compliance but presents opportunities for disciplined operators.