After CR 111, NY 281 continues northeast as a two-lane boulevard through Cortlandville, crossing into the city of Cortland for a short distance near St. Mary's Cemetery. Through Cortland, NY 281 is a two-lane residential road, bending north at Wheeler Avenue. Near Harmony Circle, NY 281 crosses out of Cortland and returns to Cortlandville, changing names from West Road to West Homer Road. A short distance after the city line, NY 281 intersects with CR 115 (Fisher Avenue). The route remains residential for a distance, passing west of Cortland Country Club and soon crossing into the town of Homer. Just after that change, the route enters an at-grade interchange with unsigned NY 930Q, which connects to I-81.