Winter oilseed rape (Brassica napus) is a global major crop used for the production of vegetable oil. Typically sown in late summer and grown throughout winter and spring, it allows for interesting cultural practices, such as frost-sensitive intercropping with companion plants. This practice not only provides nitrogen resources much needed by the crop in the spring, but companion plants can also prevent weed growth in autumn, thereby reducing common herbicide use. Additionally, intercropping has the potential to protect the crop from insect pests. During winter 2019–2020, B. napus was grown alone (i.e., as a control) or intercropped with a mixture of faba bean (Vicia faba) and grass pea (Lathyrus sativus); because of the unusually clement weather conditions, the faba bean did not freeze, which allowed for the evaluation of the impact of these companion plants on the insect pest complex in spring. Insect damage by the beetles Psylliodes chrysocephala, Ceutorhynchus napi, and Brassicogethes aeneus was assessed in both treatments. The larval density of P. chrysocephala was significantly lower in the crop grown with service plants. Egg laying and damage by C. napi were significantly reduced when B. napus was intercropped, and the number of B. aeneus captured was significantly lower in the presence of service plants than in the control. Moreover, the yield from oilseed rape was significantly higher in the part of the field with service plants than in the pure crop control. The underlying mechanisms are only partially understood, but intercropping winter oilseed rape with frost-resistant service plants seems to be an ecologically sound practice with a very high level of potential to reduce insect pest pressure and increase crop yield. This may eventually reduce our reliance on chemical inputs in one of the most treated crops.