The current development of the Internet and its growing use make it necessary to satisfy the needs of users with disabilities. The primary objective of this study is to examine healthcare-related websites in nine European countries in order to evaluate the status of their accessibility. Such a detailed statistical comparison has not yet been made in Europe, especially as the present study offers a dual measurement system combining both the application of automated testing software and statistical analysis of user feedback. The study compares 48 websites from Eastern Europe with 51 sites from Western and Northern Europe. The research phase was performed in three steps: firstly by using AChecker, secondly by Nibbler and subsequently followed by user feedback questionnaires evaluated by a group of experts. The overall goal of this study is to determine the most common accessibility problems and to draw site owners’ attention to shortcomings so that they can improve the quality of service of their healthcare-related sites in the future. The investigated European websites are grouped into Eastern and Western–Northern countries. We compared our results from different perspectives and ascertained that no significant differences can be established between the two groups predicated on their respective economic situations. Equally, no correlations were observed while comparing the sizes of web pages in Kbytes, the number of barriers and their Nibbler accessibility scores. Furthermore, there appears to be no correlation between the results of the software tests and the percentage of the elderly population in the respective country.