Background: Working horses remain essential for rural livelihoods in Chile and across Latin America. However, housing and management conditions in these systems are poorly characterized, underscoring the need for standardized welfare assessments to generate evidence and guide targeted improvements. Objective: To estimate the prevalence of abnormal behaviours in rural working horses and to examine associations with management and housing related factors. Study Design: A descriptive, cross-sectional, non-experimental study design was employed in a rural area of the Papudo commune, Valparaíso Region, Chile. A total of 77 working horses were evaluated using the Animal Welfare Indicators protocol. To analyze the relationship between behavioral abnormalities, management practices, and housing factors, a multivariable logistic regression model was applied. Results: Most horses had good body condition (67.53%, n = 53) and a low prevalence of health problems (5.19%, n = 4); however, hoof-related disorders were common (41.56%, n = 32). Housing conditions were frequently inadequate (77.92%, n = 60), with insufficient bedding in 53.25% (n = 41) and dirty bedding in 59.74% (n = 51). Only 20.78% (n = 16) of horses performed daily exercise. Overall, 29.87% (n = 23) exhibited abnormal behaviours, most commonly wood chewing (12.99%), crib-biting (10.39%), and windsucking (6.49%). Absent or inadequate bedding was associated with markedly increased odds of abnormal behaviours (OR = 5.31; p = 0.034), whereas longer daily exercise duration was protective (OR = 0.626; p = 0.007). Main Limitations: Single rural area of Chile. Several management variables (e.g., daily time out of the stall) relied on the owner report. Conclusion: A substantial proportion of rural working horses displayed abnormal behaviours. Suboptimal bedding provision and limited time out of the stall were the main modifiable factors associated with these behaviours, highlighting practical opportunities for welfare improvement in Chilean working horse systems.