Purpose: This study was undertaken to assess the associations between the anatomic outcomes of patients who underwent vitrectomy for rhegmatogenous retinal detachment associated with choroidal detachment (RRDCD) and their preoperative variables. Methods: A total of 175 patients with RRDCD who underwent vitrectomy in one eye were included in the analysis. The primary outcome measured was the retinal status after primary vitrectomy and at the end of follow-up. Results: The retinal reattachment rate was 72.57% after primary surgery, and the final total reattachment rate was 89.14% after follow-up. Binary logistic regression analysis identified that the retinal reattachment rate after primary vitrectomy was significantly associated with older age (odds ratio = 1.03, p = 0.02), mild proliferative vitreoretinopathy (PVR) (PVR grade C vs. PVR grades A-B: odds ratio = 0.31, p = 0.04; PVR grade D vs. PVR grades A-B: odds ratio = 0.03, p < 0.01), and intravitreal steroid treatment (odds ratio = 4.60, p = 0.02), and that the final retinal reattachment rate was independently associated with older age (odds ratio = 1.05; p = 0.01). Conclusions: Vitrectomy is a good surgical option for RRDCD. Older age, mild preoperative PVR, and perioperative intravitreal triamcinolone acetonide injections increase the primary reattachment rates after one operation. Older age was the only independent prognostic factor for the final retinal reattachment in patients with RRDCD.