The honey bee (Apis mellifera) is the most widely managed pollinator and is vital for crop fertilization. Recently, bee colonies have been suffering high mortality rates, exacerbated by factors such as land-use changes and the use of pesticides. Our work aimed to explore the residues of pesticides in honey-bee-collected pollen and how this contamination was affected by seasonality and the landscape composition. We selected six apiaries from different landscapes in Latvia, and pollen samples were collected during the flowering season (2023). We analyzed 39 samples and found 21 pesticide residues (mainly fungicides) with a frequency of 93 occurrences where the values were above the limit of quantification. The most frequently encountered substances were acetamiprid, boscalid, fluopyram, and prothioconazole. However, the highest concentrations were for dimoxystrobin (44 µg kg−1), acetamiprid (37 µg kg−1), azoxystrobin (27 µg kg−1), prothioconazole (25 µg kg−1), and boscalid (15 µg kg−1). We then calculated the Pollen Hazard Quotient (PHQ) for each pollen sample. No sample had a PHQ value above the critical value of 50. The highest contamination level was observed in the first half of the vegetation season (the end of May and the beginning of June), but later, it significantly decreased. We did not find any significant influence of landscape composition on pesticide pollution.