Aim This study aimed to compare the surgical outcomes of laparoscopic hysterectomy (LH) and vaginally assisted natural orifice transluminal endoscopic surgery (vNOTES) hysterectomy procedures in women with undescended-enlarged uteri. Materials and methods This cross-sectional study was conducted with 78 women who underwent LH (48 patients) or vNOTES hysterectomy (30 patients) for benign gynecological pathologies. The dimension of the uterus, operation time, intraoperative blood loss, the presence of peri-, postoperative complications, conversion to laparotomy, pre-, postoperative hemoglobin (Hb), and hematocrit (Hct) levels, postoperative hospital stay, total dose of postoperative analgesics, VAS scores at the postoperative 6th and 24th hours, and the final pathology reports were recorded. Results There was no significant difference between LH and vNOTES hysterectomy groups regarding age (47 vs. 47.5 years, p = 0.92), parity (2 vs. 2, p = 0.74), and BMI (30.8 vs. 28.2 kg/m2, p = 0.31). The patients in the vNOTES hysterectomy group had significantly shorter durations of surgery (45 vs. 160 min) and hospitalization (48 vs. 72 h) than the LH group (p < 0.001, p < 0.001, respectively). The 24th hour VAS score was lower (VAS score 2 vs. 3, p = 0.003) in favor of the vNOTES hysterectomy group. In matched group analysis, the 24th hour VAS score (2 vs. 3, p = 0.008), operation time (45 vs. 157, p < 0.001), and hospitalization (48 vs. 72, p < 0.001) were lower in the vNOTES hysterectomy group than the LH group. Conclusion vNOTES hysterectomy provides favorable outcomes compared to conventional LH considering the shorter operation time, hospitalization, and lower 24th h VAS score.