Winter annual camelina [Camelina sativa (L.) Crantz] is a freeze-hardy, early-maturing crop that allows potential for dual cropping in short-season temperate environments. However, few studies have compared winter cultivars for variation in key agronomic traits, or have addressed optimizing seeding rate for their production. Traits such as freeze hardiness and improved seed yield and quality would benefit large-scale adoption of winter camelina. The objective of this study was to compare the effects of four winter camelina cultivars (‘Joelle’, ‘Bison’, ‘HPX-WG1-35’, and ‘HPX-WG4-1’) grown at three seeding rates (334, 668, and 1000 seed m−2) on winter survival and growth, seed yield, seed oil and protein content, and fatty acid composition in west-central Minnesota. Joelle had the greatest winter survival rate, averaging 64% across three growing seasons. Plant density increased with seeding rate, but did not significantly affect seed yield. Overall, Bison yielded the greatest (944 kg ha−1) followed by Joelle (865 kg ha−1), whereas HPX-WG1-35 (650 kg ha−1) yielded the least. Both HPX-WG1-35 and HPX-WG4-1 flowered earlier than the other two cultivars and had greater seed protein content. Joelle seed had the greatest oil content, averaging 407 g kg−1, and had significantly greater oleic (C18:1) and lower linoleic acid (C18:2) contents than the other cultivars. Cultivars did not differ in erucic acid (C22:1) content, which averaged 2.2% across cultivars. Seeding at 334 seeds m−2 was sufficient to achieve maximum seed and oil yield. Variation in some key traits was identified among cultivars that may benefit breeding programs by improving winter camelina productivity and increasing its use in dual-cropping systems.