The primary aim of this research was to assess the impact of supplementing fish oil into the diet of pregnant Awassi ewes on various aspects of the dam’s productive performance, offspring birth weight, colostrum yield and quality, milk production and composition, postpartum offspring performance, and the composition of fatty acids in milk. In this study, two different fat sources, namely palm oil (PO) and fish oil (FO), were utilized, with both being included at a rate of 2.4% of dietary dry matter (DM) during the initial 65 days of gestation (early gestation stage), and then at 2.1% DM from day 65 of gestation until lambing (late gestation stage). The study subjects were Awassi ewes with a body weight (BW) averaging 57 ± 1.5 kg and an age of 3.5 ± 1.2 years. These ewes were randomly assigned to one of four dietary treatments: (i) a diet containing only palm oil from day 0 to day 150 of pregnancy (PO, n = 15); (ii) a diet containing palm oil from day 0 to day 65 of pregnancy, followed by a diet containing fish oil from day 66 to day 150 of pregnancy (POFO, n = 16); (iii) a diet containing fish oil from day 0 to day 65 of pregnancy, followed by a diet containing palm oil from day 66 to day 150 of pregnancy (FOPO, n = 16); (iv) a diet containing only fish oil from day 0 to day 150 of pregnancy (FO, n = 16). Within each treatment, ewes were housed in three replicates, with each replicate further divided into three subgroups. The first two subgroups each contained eight ewes, while the third subgroup contained nine ewes. In addition, each treatment contained 10 primiparous and 15 multiparous ewes. The results indicated that the POFO treatment led to significant increases (p < 0.05) in birth weight, gestation length, and colostrum IgG concentration. However, it also resulted in a decrease (p < 0.001) in colostrum production and a reduction (p < 0.001) in the percentage of milk fat and milk protein. Furthermore, the milk from the POFO treatment exhibited higher levels of polyunsaturated fatty acids (PUFAs) (p < 0.001) compared to the PO and FOPO treatments, while the milk saturated fatty acids (SFA) were lower (p < 0.001). In conclusion, the addition of fish oil at a rate of 2.1% DM during the late pregnancy period showed promise for enhancing birth weight, colostrum IgG concentration, and the PUFA content in the milk.