Background: Older adults have the highest rates of a sedentary lifestyle. Alpine skiing could be considered a suitable activity to encourage continued sports practice and improve the health of this population in winter. The aim of this study was to analyse the relationship between the practice of alpine skiing and health-related quality of life (HRQoL), physical self-concept (PSC), and sport motivation. Methods: The study design was cross-sectional and descriptive, involving 280 Spanish adults aged over 55 years and physically active (75.35% skiers). To assess physical activity, PSC, HRQoL, and sport motivation, we used the Rapid Assessment of Physical Activity Questionnaire (RAPA-Q), the Physical Self-Perception Profile (PSPP 30), the Health-Related Quality of Life (SF-36), and the Sport Motivation Scale (SMS) questionnaires, respectively. Results: In the skier’s group, higher values were found for PSC (p < 0.001; d = 0.64), the physical component of HRQoL (p < 0.001, d = 0.48), physical function (p < 0.001, d = 61), and intrinsic motivation (p < 0.001; d = 0.85). The practice of alpine skiing was associated with higher levels of the physical health component (ORadj = 2.13, 95% CI 1.18–3.95, p = 0.013), PSC (ORadj = 2.92, 95% CI 1.58–5.52, p < 0.001), and intrinsic motivation (ORadj = 2.24, 95% CI 1.22–4.23, p = 0.010). Conclusions: The practice of alpine skiing is positively associated with higher values of HRQoL, PSC, and intrinsic motivation, and based on the above, it seems that alpine skiing can contribute to healthy ageing and improve the quality of life of older adults.