Cesarean section rates are constantly rising, and the number of women with a prior cesarean considering a delivery mode for their next labor is increasing. We aimed to compare maternal and neonatal outcomes and feeding method in women undergoing vaginal birth after cesarean (VBAC) versus elective repeat cesarean delivery (ERCD). This was a retrospective cohort study of women with one prior cesarean delivery (CD) and no previous vaginal births, delivering vaginally or by a CD in a single institution between 2016 and 2018. 355 live singleton spontaneous vaginal and cesarean deliveries were included. 121 women delivered vaginally and 234 had a CD. Neonates born by a CD were more likely to have higher birth weight (p < 0.001), higher weight at discharge (p < 0.001), macrosomia (p = 0.030), lose >10% of their body mass (p = 0.001), be mixed-fed (p < 0.001), and be hospitalized longer (p < 0.001). Children born vaginally were more likely to be exclusively breastfed (p < 0.001). Women undergoing VBAC were more likely to deliver preterm (p = 0.006) and post-term (p < 0.001), present with PROM (p < 0.001), have greater PROM latency period (p < 0.001), and experience intrahepatic cholestasis of pregnancy (p = 0.029), postpartum anemia (p < 0.001), and peripartum blood loss >1 L (p = 0.049). The incidence of anemia during pregnancy was higher in the ERCD cohort (p = 0.047). Women undergoing VBAC are more likely to breastfeed their children, perhaps for the same reason they choose the vaginal method of delivery, as vaginal delivery and breastfeeding along with antibiotic use, are the most important factors decreasing the risk for future diseases in their offspring.