Hypertension and atherosclerotic cardiovascular diseases (ASCVD) increase cardiovascular risk and worsen patients' prognoses. One early predictor of increased risk is a change in arterial stiffness. This study aimed to evaluate arterial stiffness parameters using the non-invasive photoplethysmography (PPG) method in Polish patients with arterial hypertension (AH) and/or atherosclerosis (AS). The study group consisted of 333 patients (Caucasians, both sexes, aged 30-85 years old). Patients were analyzed in four groups depending on AH and AS (Group I: patients without AH or AS, Group II: AH patients, Group III: AS patients, and Group IV: AH/AS patients) and, in addition, according to sex and history of SARS-CoV-2 infection. Arterial stiffness parameters, i.e., reflection index (RI), peak-to-peak time (PPT), and stiffness index (SI) were automatically calculated with PPG based on the analysis of the pulse wave contour. Mean values of RI and SI were higher in men than women (p < 0.001 each). Diastolic blood pressure (DBP) also differed between sexes (p = 0.010). Mean SI values differed between the study groups (p = 0.038) with the highest SI found in AS/AH patients and the lowest-in patients without AH or AS. The mean SI values were significantly lower in women compared to men in both Group I and Group II (p = 0.006 and p < 0.001, respectively). The mean values of RI were also greater in men than in women in Group I and Group II (p < 0.001 for each group). Regarding COVID-19 history, only HR values differed between patients with and without COVID-19 in AH patients (p = 0.012). In AH patients, men had higher values of RI and SI compared to women (p < 0.001 and p < 0.001). On the other hand, AS women with COVID-19 had significantly greater mean values of SI (9.66 m/s ± 1.61) than men with COVID-19 (7.98 m/s ± 1.09) (p = 0.045). The present study confirmed that sex had a significant impact on arterial stiffness parameters. Both AH and AS affected arterial stiffness. Heart rate was greater in hypertensive patients after COVID-19 compared to hypertensive patients without COVID-19.