The abrupt interruption of face-to-face educational activities imposed by the Italian government in response to the COVID-19 pandemic required a rapid switch to distance learning to guarantee continuity in education. The same applied to the School-in-Hospital (SiHo) services. This paper explores the impact of the COVID-19 pandemic in this specific context; we investigated the organizational changes and strategies adopted by the SiHo services and individual teachers to meet the challenges posed by this change in the educational paradigm. Moreover, the paper outlines teachers’ visions about possible educational scenarios for the next academic year (2020–2021). Using qualitative methodology, the study took the form of a group interview involving 12 teachers working across 8 children’s hospitals in Italy. The thematic analysis revealed a number of themes for further investigation. In terms of the actual situation during the pandemic, we identified critical issues and facilitating factors that occurred in distance learning with hospitalized students. One significant theme that emerged from the interviewees’ narratives involved their general attitudes towards distance learning and their individual approaches to the pandemic. The relationship of hospitalized students to mainstream schools also proved to be an important theme, not only regarding the recent past but also the future. Finally, teachers hypothesized future distance learning scenarios for the new school year, highlighting the challenges to be faced from several viewpoints (methodological, organizational, technological, etc.).