A cross-sectional study investigated risk factors associated with choices to drink bottled water and tap water in rural Saskatchewan. Of 7,500 anonymous postal questionnaires mailed out, 2,065 responses were analyzed using generalized linear mixed models. Those who reported a water advisory (p < 0.001) or living in the area for £10 years (p = 0.01) were more likely to choose bottled water. Those who reported tap water was not safe to drink were more likely to choose bottled water, an effect greater for those who had no aesthetic complaints (p ≤ 0.001), while those with aesthetic complaints were more likely to choose bottled water if they believed the water was safe (p < 0.001). Respondents who treated their water and did not use a community supply were more likely to choose bottled water (p < 0.001), while those who did not treat their water were more likely to choose bottled water regardless of whether a community supply was used (p < 0.001). A similar pattern of risk factors was associated with a decreased likelihood of consuming tap water daily; however, the use of a community water supply was not significant. Understanding the factors involved in drinking water choices could inform public health education efforts regarding water management in rural areas.