There is increasing evidence linking early life adiposity to disease risk later in life. This study aims at determining the prevalence and correlates of overweight and obesity among preschoolers in Lebanon. A national cross-sectional survey was conducted amongst 2–5 years old children (n = 525). Socio-demographic, lifestyle, dietary, and anthropometric data were obtained. The prevalence of overweight and obesity was estimated at 6.5% and 2.7%, respectively. Based on stepwise logistic regression for the prediction of overweight and obesity (combined), the variance accounted for by the first block (socioeconomic, parental characteristics) was 11.9%, with higher father’s education (OR = 5.31, 95% CI: 1.04–27.26) and the presence of household helper (OR = 2.19, 95% CI: 1.05–4.56) being significant predictors. The second block of variables (eating habits) significantly improved the prediction of overweight/obesity to reach 21%, with eating in front of the television (OR = 1.07, 95% CI: 1.02–1.13) and satiety responsiveness (OR = 0.83, 95% CI: 0.70–0.99) being significantly associated with overweight/obesity. In the third block, fat intake remained a significant predictor of overweight/obesity (OR = 2.31, 95% CI: 1.13–4.75). This study identified specific risk factors for preschool overweight/obesity in Lebanon and characterized children from high socioeconomic backgrounds as important target groups for preventive interventions. These findings may be of significance to other middle-income countries in similar stages of nutrition transition.