Background: Tdap and flu immunization in pregnancy has been proven to be both effective and safe. Despite this, the vaccination rate in pregnant women is low in Italy. The COVID-19 pandemic has focused the attention of public opinion on communicable diseases, underlining the importance of primary prevention measures such as vaccination. We conducted a survey to investigate the behavior of pregnant women during the COVID-19 pandemic regarding maternal immunization to identify the reasons for vaccine hesitancy in order to overcome them. The new challenge is COVID-19 vaccination in pregnancy, and preliminary data show hesitancy towards it. Our analysis may be useful to improve immunization in the pregnant population, including through the COVID-19 vaccine. Methods: A targeted survey was performed in Italy including 520 women who experienced in the first trimester of pregnancy, prior to the novel coronavirus spread, the 2019–2020 influenza vaccination campaign and the Tdap vaccine recommendation in the third trimester during the COVID pandemic. They represent a unique model to investigate if the new coronavirus outbreak might have changed attitudes towards vaccination in pregnancy in the same patients. Data were collected from a self-completed paper questionnaire. Descriptive statistics were calculated and percentages were compared using the chi-2 test or Fisher’s exact test. Results: We obtained data from 195 of the 520 women who gave birth during the inclusion period; 325 cases declined to participate in the survey. A total of 8.7% (17 cases) performed flu vaccination in the first trimester of pregnancy (pre-COVID era), 50.8% (99 cases) accepted Tdap immunization during their third trimester of gestation (COVID-19 pandemic) and 6.7% (13 cases) received both vaccines during pregnancy. For both the flu and Tdap shots, pregnant patients were more likely to accept the vaccines if they were recommended by a healthcare provider, whereas the main reason not to be vaccinated was the lack of such a recommendation. Conclusions: Our survey shows that the COVID-19 experience, which has raised awareness as to the role of vaccines in preventable diseases, may positively change attitudes toward immunization in pregnancy. Vaccination must be recommended to all pregnant women and organized during routine prenatal care as an important element for the prevention of communicable diseases. Vaccination hesitancy can be minimized through consistent recommendation to all pregnant women offered by obstetric staff during routine prenatal care. This approach is likely to be effective in terms of building trust in flu and Tdpa immunization among pregnant women, as well as to avoid unjustified hesitancy towards the more recent COVID-19 vaccines.