A growing body of evidence highlights that the COVID-19 pandemic affected oneiric activity. However, only a few studies have assessed the longitudinal changes in dream phenomenology during different phases of the pandemic, often focused on a limited number of dream variables. The aim of the present study was to provide an exhaustive assessment of dream features during total lockdown (TL) and a post-lockdown (PL) period characterized by eased restrictive measures in Italy. We performed a longitudinal study using a web-based survey to collect demographic, COVID-19 related, clinical, sleep, and dream data at TL and PL. Our final sample included 108 participants. The high frequency of poor sleep quality, anxiety, and depressive symptoms observed during TL remained stable at PL, while sleep latency (t = −4.09; p < 0.001) and PTSD-related disruptive nocturnal behaviors (t = −5.68; p < 0.001) exhibited a reduction at PL. A PL decrease in time spent with digital media was observed (t = −2.77; p = 0.007). We found a strong PL reduction in dream frequency (t = −5.49; p < 0.001), emotional load (t = −2.71; p = 0.008), vividness (t = −4.90; p < 0.001), bizarreness (t = −4.05; p < 0.001), length (t = −4.67; p < 0.001), and lucid dream frequency (t = −2.40; p = 0.018). Fear was the most frequently reported emotion in dreams at TL (26.9%) and PL (22.2%). Only the frequency of specific lockdown-related dream contents exhibited a reduction at PL. These findings highlight that the end of the home confinement had a strong impact on the oneiric activity, in the direction of reduced dream frequency, intensity, and lockdown-related contents. The co-occurrence of such changes with a decline in nocturnal PTSD-related symptoms, sleep latency, and time with digital media suggests an influence of post-traumatic stress levels, lifestyle modifications, and sleep pattern on dream changes during different phases of the pandemic. The stable prevalence of fear in dreams and the large frequency of poor sleep quality, depressive symptoms, and anxiety are probably related to the persistence of many negative consequences of the pandemic. Overall, these results are consistent with the continuity hypothesis of dreams.