•Associations between weather conditions and cycling are explored in Rotterdam.•Temperature has supportive effects, wind and precipitation show inhibitory effects.•Relationships are stronger for leisure than work trips.•Residential location matters and influences weather effects on mode choices.•Local models outperform region-wide counterparts. With its sustainability, health and accessibility benefits, cycling has nowadays been established on research and policy agendas. Notwithstanding the decision to cycle is closely related to local weather conditions and interwoven with the geographical context, research dealing with both aspects is scarce. On the basis of travel diary data, we assess the association of three weather conditions, namely air temperature, wind speed, and precipitation, on cycling trips for leisure and commute purposes for the Greater Rotterdam area, the Netherlands. Besides region-wide logit models and autologistic regressions, place-specific associations of weather conditions are explored through geographically weighted logit models. Considering the entire Rotterdam area, results confirm significant weather effects on cycling while highlighting the necessity to model the residents’ locational component. When the confounding effects of individual and household characteristics are controlled, a key finding is that weather effects appear to vary across space, specifically between the more densely settled central environments and the surrounding lower-density areas. Additionally, the results show differences between leisure and commute trips, in which leisure trips appear to be more weather sensitive and show more pronounced spatial patterns.