Haematological patients are more susceptible to infections. Vaccination has always been the most effective primary prevention strategy, even during the COVID-19 pandemic. However, the efficacy of vaccines for some haematological patients is low. Although vaccination of Healthcare Workers (HCWs) could protect patients from vaccine-preventable diseases, there is evidence of a high level of hesitation among healthcare workers in Italy. The aim of this study was to explore the attitudes towards vaccination of HCWs caring for haematology patients. Qualitative descriptive design was conducted. Twenty-one HCWs were interviewed. Content analysis was applied to the qualitative data. The following themes were generated from the analysis: “Trust”, “Decision-making process focusing on individual health”, “Decision-making process focusing on community health”, “Changing opinion”, and “Two sides of vaccination commitment”. The most hesitant HCWs were oriented towards individual health. They perceived a lack of benefit from vaccines, feared side effects, or were influenced by negative experiences of others. In contrast, community-health-oriented HCWs showed more positive attitudes towards vaccination. Some hesitant HCWs changed their opinion on vaccination because they began to reflect on the importance of vaccination for the community. The change in opinion of some HCWs interviewed provided insight into the importance of focusing organisational efforts on collective responsibility.