Developments such as climate change and a growing demand for drinking water threaten the sustainability of drinking water supply worldwide. To deal with this threat, adaptation of drinking water supply systems is imperative, not only on a global and national scale but particularly on a local scale. This investigation sought to establish characteristics that describe the sustainability of local drinking water supply. The hypothesis of this research was that sustainability characteristics depend on the context that is analysed, and therefore, a variety of cases must be analysed to reach a better understanding of the sustainability of drinking water supply in the Netherlands. Therefore, three divergent cases on drinking water supply in the Netherlands were analysed. One case related to a short-term development (2018 summer drought), and two concerned long-term phenomena (changes in water quality and growth in drinking water demand). We used an integrated systems approach, describing the local drinking water supply system in terms of hydrological, technical, and socio-economic characteristics that determine the sustainability of a local drinking water supply system. To gain a perspective on the case study findings that are broader than the Dutch context, the sustainability aspects identified were paired with global aspects concerning sustainable drinking water supply. This resulted in the following set of hydrological, technical, and socio-economic sustainability characteristics: (1) water quality, water resource availability, and impact of drinking water abstraction; (2) reliability and resilience of the technical system and energy use and environmental impact; (3) drinking water availability, water governance, and land and water use. Elaboration of these sustainability characteristics and criteria into a sustainability assessment can provide information on the challenges and trade-offs inherent in the sustainable development and management of a local drinking water supply system.