The COVID-19 pandemic has had a significant long-term impact on education worldwide. In many countries, schools and universities experienced a rapid switch to emergency remote teaching and learning (ERTL), which affected many education systems in the 2020–21 school year. This was true for the Italian educational context as a whole, including School in Hospital (SiHo) services. This study explored how the SiHo functioned in Italy during the 2020–2021 school year. The aim was to explore what, if any, changes the emergency brought about in educational practices and in the adoption of technologies in this specific context, with a particular focus on any differences between school levels. The study was conducted with 252 SiHo teachers using a questionnaire format. The results showed that after the forced adoption of distance modes during the spring 2020, face-to-face teaching returned to be the prevalent mode in the 2020–2021 school year, with some exceptions for upper-secondary school students (covered by ministerial provisions). The teaching approach that SiHO teachers prefer, both for face-to-face and distance lessons, remains frontal instruction, probably given the particular needs of their students. Younger students probably experienced the most significant changes due to the limits imposed on interpersonal contact in hospitals, which prevented group work and play, previously commonly adopted by kindergarten and primary school teachers. In terms of technology integration in educational practice, teachers stated that they had acquired greater competence in the use of a variety of technological resources.