Background/Objectives: Sleep disturbance is often observed in the context of chronic pain. We hypothesize that, by providing an immersive Virtual Reality (VR) experience with a serious game to chronic pain patients an hour before bedtime, attention can be diverted from the pain condition, consequently leading to improved sleep quality. The aim is to evaluate the efficacy of VR compared to usual care in reducing the number of awakenings during the night and increasing sleep efficiency in patients suffering from painful diabetic polyneuropathy (PDPN). Methods: Eight patients with PDPN were randomized to either two weeks of VR or two weeks of usual care, followed by a cross-over. The primary outcome measurements were sleep efficiency and number of awakenings during the night. As secondary outcomes, self-reported sleep quality, insomnia, pain catastrophizing, anxiety, depression, pain intensity, side effects and impression of change were evaluated. Results: Data of seven patients were analysed. Actigraphy data, self-reported sleep quality, insomnia, pain catastrophizing, anxiety, depression and pain intensity scores did not differ between usual care and VR. As for impression of change, more patients improved after VR compared to usual care (V = 21, p = 0.03). Conclusions: A 2-week period of pain neuroscience education through VR did not result in increased sleep efficiency or fewer awakenings compared to usual care in patients with PDPN. These pilot results indicate that patients subjectively experience an improvement, yet this is not substantiated by either self-reported or objective measurements.