Background/Objectives: Multidrug-resistant urinary tract infections (MDR UTIs) constitute an important public health problem, especially in pregnant patients. The aim of this retrospective study was to characterize the bacterial spectrum and the profile of microbial resistance in cases of UTIs occurring in pregnant women, as well as their impact on obstetrical and neonatal outcomes. Methods: A total of 371 pregnant patients with UTIs were included in the analysis and were segregated into the following groups based on the type of bacterial resistance to antibiotics: MDR UTIs (70 patients, group 1), UTIs resistant to one class of antibiotics (108 patients, group 2), UTIs resistant to two classes of antibiotics (102 patients, group 3), and sensitive UTIs (91 patients, group 4). We used descriptive statistics for characterizing and comparing the microbial spectrum and the clinical characteristics of the patients. A multinomial logistic regression model for evaluating the relationship between the type of urinary tract infection and adverse obstetric or neonatal outcomes was employed. Results: In the case of MDR UTIs, the bacterial spectrum mainly included Escherichia coli, Enterococcus faecalis, and Klebsiella species. We found almost universal resistance to ampicillin. Our data confirmed an increased risk of preterm birth, premature rupture of membranes, neonatal respiratory distress syndrome, and neonatal intensive care unit admission for patients with MDR infections. Conclusions: The increased incidence of pathogens resistant to commonly used antibiotic classes in pregnancy suggests the need for the development of local and national protocols that adapt therapeutic and prophylactic regimens to clinical realities.