The emergency presented through the COVID-19 pandemic exposed the need to adopt remote, technology-driven solutions and make healthcare services more resilient. To do so, we need technological applications (i.e., telemedicine) that are designed and tailored to the end-users (i.e., chronic patients) needs and the type of healthcare service they get (i.e., cancer care). The requirements above are especially relevant to Greece, being a country with numerous sparsely populated regions (e.g., islands, regions at the borders) and a deteriorating access to healthcare for all citizens. Trying to address such diverse problems and needs, there have been multiple, different telemedicine and telecare projects in Greece in the past years. To support the future design and implementation of such endeavours, in this study we translated a questionnaire measuring the acceptance of telemedicine by patients and adapted it to the Greek context. We continued by running a small-scale pilot with 73 Greek women with breast cancer to assess the adapted instrument for its reliability and construct validity. The created questionnaire had good overall and internal reliability scores for most sub-scales. Factor analysis did not identify the same number of latent dimensions as the original theoretical model. Reverse wording items needing to be recoded were identified, and items that could be omitted in future versions of the questionnaire. Increasing the sample size for the purposes of a longitudinal study, the construct, convergent, and discriminant validity are elements to be further examined in future studies. It is envisaged that the creation of this questionnaire will support the adoption of telemedicine by Greek healthcare services into more routine areas of patient care provision.