The Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2) pandemic significantly impacted the general population’s health. At times, the infection has unfavorably influenced pregnancy evolution and the result of birth. However, vertical transmission of the virus is rare and generates controversial discussions. The study aimed to highlight the clinical, laboratory, and imaging findings of pregnant women with confirmed Coronavirus Disease 2019 (COVID-19) with possible vertical transmission and identify possible factors that encourage vertical transmission. Between 1 April 2020 and 31 December 2021, 281 pregnant women diagnosed with COVID-19 gave birth in the Obstetrics and Gynecology Departments of the tertiary unit of County Emergency Clinical Hospital from Timisoara. Three newborns (1.06%) tested positive. The characteristic of these three cases was described as a short series. In two cases, the patients were asymptomatic. In one case, the patient developed a mild form of COVID-19 with a favorable evolution in all cases. We did not identify the presence of smoking history, vaccine before admission, atypical presentation, fever, or chest X-ray abnormalities. We note possible factors that encourage vertical transmission: Pregnancy-induced hypertension, thrombophilia, asymptomatic cough, an asymptomatic or mild form of the disease, a ruptured membrane, and cesarean. The laboratory results highlight the inconstant presence of some changes found in the list of potential predictors of the severity of the infection: Lymphopenia, high values of C-reactive protein, D-dimer, fibrinogen, platelets, Aspartate Aminotransferase, Lactate dehydrogenase, and ferritin. The study’s conclusion of this small group suggests that there may have been an intrauterine infection in late pregnancy and described characteristics of the pregnant women. Possible risk factors that could encourage vertical transmission have been identified.