Background: Virtual reality viewed using a head-mounted display (HMD-VR) has the potential to be a useful tool for motor learning and rehabilitation. However, when developing tools for these purposes, it is important to design applications that will effectively transfer to the real world. Therefore, it is essential to understand whether motor skills transfer between HMD-VR and conventional screen-based environments and what factors predict transfer. Methods: We randomized 70 healthy participants into two groups. Both groups trained on a well-established measure of motor skill acquisition, the Sequential Visual Isometric Pinch Task (SVIPT), either in HMD-VR or in a conventional environment (i.e., computer screen). We then tested whether the motor skills transferred from HMD-VR to the computer screen, and vice versa. After the completion of the experiment, participants responded to questions relating to their presence in their respective training environment, age, gender, video game use, and previous HMD-VR experience. Using multivariate and univariate linear regression, we then examined whether any personal factors from the questionnaires predicted individual differences in motor skill transfer between environments. Results: Our results suggest that motor skill acquisition of this task occurs at the same rate in both HMD-VR and conventional screen environments. However, the motor skills acquired in HMD-VR did not transfer to the screen environment. While this decrease in motor skill performance when moving to the screen environment was not significantly predicted by self-reported factors, there were trends for correlations with presence and previous HMD-VR experience. Conversely, motor skills acquired in a conventional screen environment not only transferred but improved in HMD-VR, and this increase in motor skill performance could be predicted by self-reported factors of presence, gender, age and video game use.