Background: Despite the implementation of Enhanced Recovery After Surgery (ERAS) programs, surgical stress continues to influence postoperative rehabilitation, including the period after discharge. However, there is a lack of data available beyond the point of discharge following video-assisted thoracoscopic surgery (VATS) wedge resection. Therefore, the objective of this study is to investigate incidence and risk factors for readmissions after ERAS VATS wedge resection. Methods: A retrospective analysis was performed on data from prospectively collected consecutive VATS wedge resections from June 2019 to June 2022. We evaluated main reasons related to wedge resection leading to 90-day readmission, early (occurring within 0–30 days postoperatively) and late readmission (occurring within 31–90 days postoperatively). To identify predictors for these readmissions, we utilized a logistic regression model for both univariable and multivariable analyses. Results: A total of 850 patients (non-small cell lung cancer 21.5%, metastasis 44.7%, benign 31.9%, and other lung cancers 1.9%) were included for the final analysis. Median length of stay was 1 day (IQR 1–2). During the postoperative 90 days, 86 patients (10.1%) were readmitted mostly due to pneumonia and pneumothorax. Among the cohort, 66 patients (7.8%) had early readmissions primarily due to pneumothorax and pneumonia, while 27 patients (3.2%) experienced late readmissions mainly due to pneumonia, with 7 (0.8%) patients experiencing both early and late readmissions. Multivariable analysis demonstrated that male gender, pulmonary complications, and neurological complications were associated with readmission. Conclusions: Readmission after VATS wedge resection remains significant despite an optimal ERAS program, with pneumonia and pneumothorax as the dominant reasons. Early readmission was primarily associated with pneumothorax and pneumonia, while late readmission correlated mainly with pneumonia.