Background: This cross-sectional survey investigated the knowledge, attitudes, and coverage of recommended vaccinations among a random sample of patients with chronic medical conditions, at higher risk of vaccine-preventable diseases (VPDs), in Italy. Methods: The survey was conducted via telephone-based interviews. Results: Multinomial regression analysis showed that the patients who believed that VPDs were severe were more likely to know one recommended vaccination; those who believed that VPDs were severe and those who were advised from a general practitioner (GP) were more likely to know two vaccinations; those who were older, graduated, with more time from diagnosis, who believed that VPDs were severe, who did not need additional information, and who were advised from a GP were more likely to know three or four vaccinations. Patients who knew at least one vaccination, who perceived themselves at risk, and who were advised from a GP were more likely to have received one vaccination; those who knew more than one vaccination and who were advised from a GP were more likely to receive two or three vaccinations. Among the unvaccinated, patients who were unmarried/not cohabiting, those who needed information, and who believed that vaccinations were useful and safe were more willing to receive the recommended vaccinations. Conclusions: Educational interventions are needed to improve the adherence of individuals with chronic medical conditions.