Background/Objectives: Parkinson’s disease (PD) and hypertension are often coexistent conditions that interact in entwined ways at various levels. Cardiovascular autonomic dysfunction (CAD), a non-motor feature of PD occurring across all stages, alters blood pressure (BP) regulation. Methods: We conducted a cross-sectional study enrolling patients with PD and primary hypertension, without diabetes mellitus or other causes of secondary CAD, aiming to characterize BP profiles/patterns by ambulatory BP monitoring. We also sought associations between different CAD phenotypes and PD characteristics, disability, and cardiovascular comorbidities. Results: We included 47 patients with a median age of 71 years, PD duration of 9 years, and Movement Disorder Society-sponsored revision of the Unified Parkinson’s Disease Rating Scale (MDS-UPDRS) Part III score of 40. Diurnal and nocturnal BP values were within the reference range, but BP load was excessive. Almost one-third had neurogenic orthostatic hypotension (OH) and 80% were non-dippers. The overall burden of non-motor symptoms was significant in these phenotypes. Patients with neurogenic OH were more prone to constipation, anxiety, and urinary problems, whereas gustatory dysfunction, loss of libido, and erectile dysfunction were more frequently reported by non-dippers. No significant differences with regard to cognitive decline were identified in subjects with and without neurogenic OH. Neurogenic OH was symptomatic in 78% of the cases, whereas 56% of those with orthostatic symptoms did not have OH at repeated measurements. Conclusions: Neurogenic OH is an independent predictor of disability in patients with PD and hypertension, after adjusting for PD duration, Hoehn and Yahr stage, levodopa equivalent daily dose (LEDD), and Montreal Cognitive Assessment (MoCA) score.