Teaching relevant social skills during engagement with leisure activities may promote natural interactions and enhance the benefits of leisure. The present study evaluated the effect and generalization of a treatment hierarchy starting with a video modeling and video feedback package (VMVF) for teaching social skills to adolescents with autism during leisure. Participants were between the ages of 15 and 21 with ASD and attended a residential school. Six target social skills determined to be important in typical leisure based interactions were divided into three domains: (a) initiating joint participation, (b) conversation relevant to activities, and (c) prosocial interactions. Experimental control was demonstrated using a multiple-baseline within participants design. Participants were shown one of the video models twice successively at the start of the session. Following the session, participants were shown the video recording and given feedback in the form of praise or suggestions for improvement. Additional treatment components of the package included naturalistic prompting and arbitrary reinforcers. Although VMVF alone had limited success, the additional treatment components produced an increase in targeted social skills. Interobserver agreement was calculated in 40% of sessions with a score of 94%.