Background Telemonitoring could offer solutions to the mounting challenges for health care and could improve patient self-management. Studies have addressed the benefits and challenges of telemonitoring for certain patient groups. Objective This paper will examine the nationwide uptake of telemonitoring in chronic care in the Netherlands from 2014 to 2019 by means of an annual representative survey among patients and health care professionals. Methods Between 2014 and 2019, approximately 2900 patients with chronic diseases, 700 nurses, and 500 general practitioners (GPs) and medical specialists received a questionnaire. About 30 questions addressed topics about the use of eHealth and experiences with it, including data about telemonitoring. Results Between 2014 and 2019, the use of telemonitoring remained stable for all groups except medical specialists. In medical specialist departments, the use of telemonitoring increased from 11.2% (18/161) in 2014 to 19.6% (36/184) in 2019 (χ24=12.3; P=.02). In 2019, telemonitoring was used by 5.8% (28/485) of people with chronic disease. This was 18.2% (41/225) in GP organizations and 40.4% (44/109), 38.0% (78/205), and 8.9% (29/325) in the organizations of nurses working in primary, secondary, and elderly care, respectively. Up to 10% of the targeted patient group such as diabetics were regarded by health care professionals as suitable for using telemonitoring. The main benefits mentioned by the patients were “comfort” (421/1043, 40.4%) and “living at home for longer/more comfortably” (334/1047, 31.9%). Health care professionals added “improvement of self-management” (63/176, 35.8% to 57/71, 80.3%), “better understanding of the patient’s condition” (47/176, 26.7% to 42/71, 59.2%), “reduction of workload” (53/134, 39.6% of nurses in elderly care), “better tailoring of care plan to the patient’s situation” (95/225, 42.2% of GPs), and “saves time for patients/caregivers” (61/176, 34.7% of medical specialists). Disadvantages mentioned by professionals were that “it takes time to monitor data” (13/130, 10% to 108/225, 48.0%), “it takes time to follow up alerts” (15/130, 11.5% to 117/225, 52.0%), and “it is difficult to estimate which patients can work with telemonitoring” (22/113, 19.5% to 94/225, 41.8%). Conclusions The uptake of telemonitoring in Dutch chronic care remained stable during 2014-2019 but increased among medical specialists. According to both patients and professionals, telemonitoring improves the quality of life and quality of care. Skills for suitably including eligible patients and for allocating the tasks of data monitoring and follow-up care within the team would help to further increase the use of telemonitoring.