Background: Both preterm and post-term births have been associated with neonatal morbidity and mortality, including adverse impact on neurodevelopment. Important neural maturational processes take place during sleep in newborns, but findings on gestational duration and sleep in early childhood are contradictory and often derive from small clinical samples. We studied the association of gestational age at birth with sleep duration in early childhood in three population-based cohorts. Methods: Gestational age at birth and sleep duration were assessed in three population-based cohort studies in The Netherlands (n = 6471), Singapore (n = 862), and Canada (n = 583). Gestational age at birth was assessed using ultrasound in pregnancy in combination with date of birth, and caregivers repeatedly reported on child sleep duration at three, six, 24, and 36 months of age. Generalized estimating equations were used, which were adjusted for confounders, and findings were pooled in a meta-analysis. Results: Children born preterm (<37 weeks of gestation) showed longer sleep duration than children born at term; and children born post-term (≥42 weeks of gestation) showed shorter sleep duration. The meta-analysis indicated a small negative effect of gestational age on child sleep duration (effect size −0.11), when assessed in children born at term only. Conclusion: In early childhood, children with a lower gestational age have a longer sleep duration, even when they are born at term (37–42 weeks of gestation). These subtle yet consistent findings point to the importance of maturational processes during sleep, not only in premature children but also in children born at term after shorter gestational duration.