We carried out a qualitative and quantitative analysis of the phytochemical composition of the fruits of large cranberry cultivars ‘Ben Lear’, ‘Bergman’, ‘Kalnciema agra’, ‘Lemunyon’, ‘Pilgrim’, ‘Stevens’, and ‘Tina’ grown in Latvian climatic conditions. The following predominant compounds were found in cranberry fruit samples: peonidin-3-O-galactoside, peonidin-3-O-arabinoside, cyanidin-3-O-galactoside, cyanidin-3-O-arabinoside, myricetin-3-galactoside, quercetin-3-galactoside, quercetin-3-α-L-arabinofuranoside, quercetin 3-rhamnoside, ursolic acid, and oleanolic acid. During the berry ripening period (from 16 August until 15 September), a trend of decreasing amounts of compounds was found in the fruit samples of the studied cranberry cultivars: the total amount of proanthocyanidins decreased by 1.3 times, the total amount of the identified flavonols decreased by 1.3 times, the total amount of triterpenoids decreased by 1.2 times, and the total amount of chlorogenic acid decreased by 1.7 times. During the period from 16 August until 15 September, the total amount of anthocyanins in the cranberry fruit samples increased by 2.6 to 17 times. The highest total amount of anthocyanins (5305.80 ± 27 µg/g) was detected in fruit samples of the cranberry cultivar ‘Kalnciema agra’ collected on 15 September. The amount of biologically active compounds in cranberry fruit samples varies during berry ripening. Thus, the choice of the picking time is one of the factors that determines the phytochemical composition of raw cranberry material.