Winter tourism is often associated with rural areas and snow-based sporting activities. However, urban destinations can also offer outdoor winter sports and an integrated set of urban tourism product bundles not only sports-related. Previous research has strongly focused on highly developed rural winter sports destinations but has barely explored the case of urban destinations offering winter sports as an integrated activity in their urban tourism product bundles. This paper, therefore, investigates the potential for market innovations that combine urban assets with winter sports activities by segmenting urban winter sports tourists and extending the understanding of urban tourism attractiveness. This paper identifies skiers’ motivation factors for visiting urban destinations with a winter sports infrastructure. It builds on a three-step quantitative approach (N = 338) with factor analysis, cluster analysis and posthoc testing to compare cluster means. The results highlight five push (exciting, knowledge, relaxation, achievement and family) and six pull factors (basic assets, urban assets, natural scenery, social events, economic aspects and winter sports activities), which can be clustered into three unique and statistically different groups: “moderate skiers”, “urban recreational skiers” and “focused skiers”. Addressing these identified clusters highlights the market potential of bundling winter sports and urban tourism, thereby addressing customers who have not been of strategic relevance for winter destinations. Additionally, urban winter destinations can gain a unique selling proposition and help to counteract crowding tendencies in rural alpine winter sports while also improving urban destination attractiveness post-COVID-19.