Background/Objectives: Bowel endometriosis (BE) is characterized by the presence of endometrial-like tissue within the muscular layer of the bowel wall. When BE does not result in the severe obstruction to fecal transit and in the absence of (sub)occlusive symptoms, the decision to perform surgery can be challenging, as intestinal procedures are associated with higher complication rates and long-term bowel dysfunction. This cross-sectional study aims to evaluate the quality of life (QoL) in patients with BE who avoided surgery, as well as to investigate the impact of the characteristics of BE nodules on the QoL and intestinal function. Methods: A retrospective cross-sectional analysis was conducted involving 580 patients with BE who did not undergo surgery but were treated conservatively with medical therapy or expectant management between January 2017 and August 2022. The diagnosis of BE was established through transvaginal ultrasound and confirmed via double contrast barium enema. After at least one year of follow-up, the QoL and intestinal function were assessed using the Endometriosis Health Profile-5 (EHP-5) questionnaire and the Bowel Endometriosis Symptom (BENS) score, while pain symptoms were quantified with the Visual Analog Scale (VAS 0–10). Statistical analyses were performed to explore potential associations between the QoL and the characteristics of BE nodules (size, location, and evidence of stenosis), as well as the type and duration of medical therapy. Results: Patients with BE reported a satisfactory overall QoL, with a mean EHP-5 score of 105.42 ± 99.98 points and a VAS score below three across all pain domains. They did not demonstrate significant impairment in bowel function, as indicated by a mean BENS score of 4.89 ± 5.28 points. Notably, patients receiving medical therapy exhibited a better QoL compared to those not receiving treatment (p < 0.05), with the exception of postmenopausal patients, who reported the highest QoL overall (p < 0.05). Among the characteristics of BE, nodule location significantly impacted the QoL and symptom intensity, with low (rectal or rectosigmoid) nodules less tolerated compared to sigmoid nodules, particularly regarding non-menstrual pelvic pain (NMPP), dyschezia, and psychological impact on daily life (p < 0.05). Conclusions: Women can effectively manage BE conservatively in the absence of (sub)occlusive symptoms, even when large nodules are present, causing significant radiological stenosis. The characteristics of BE nodules do not significantly affect the QoL or symptom intensity; however, the location of BE nodules is a crucial factor negatively influencing these outcomes. Medical therapy may confer a beneficial impact on patients of reproductive age with BE, but its use should be carefully considered for those approaching menopause, weighing the risks and benefits.