Recent studies report that cybersecurity breaches noticed in hospitals are associated with low levels of personnel’s cybersecurity awareness. This work aims to assess the cybersecurity culture in healthcare institutions from middle- to low-income EU countries. The evaluation process was designed and performed via anonymous online surveys targeting individually ICT (internet and communication technology) departments and healthcare professionals. The study was conducted in 2019 for a health region in Greece, with a significant number of hospitals and health centers, a large hospital in Portugal, and a medical clinic in Romania, with 53.6% and 6.71% response rates for the ICT and healthcare professionals, respectively. Its findings indicate the necessity of establishing individual cybersecurity departments to monitor assets and attitudes while underlying the importance of continuous security awareness training programs. The analysis of our results assists in comprehending the countermeasures, which have been implemented in the healthcare institutions, and consequently enhancing cybersecurity defense, while reducing the risk surface.