Overwintering frost damage is a major challenge for the wine grape industry in northern China. This study investigates overwintering treatments to improve survival rates and mitigate frost damage in the wine grape production area of the northern foothills of the Tianshan Mountains. Seven overwintering treatments were tested: soil-covered striped cloth, striped cloth, sandwiched striped cloth, thickened striped cloth, double-layered striped cloth, heat-insulating striped cloth, and heat-insulating sandwich striped cloth. Temperature and humidity were continuously monitored during the overwintering period, both aboveground and at depths of 20 and 40 cm underground. By analyzing temperature trends, the duration of low temperatures, and temperature fluctuations, comprehensive overwintering indices were derived through principal component analysis to assess heat retention, moisture preservation, and the impact on grapevine survival. The results showed that the sandwiched striped cloth treatment provided the best insulation, with a 4.4 °C higher minimum daily temperature and a 356% increase in overwintering indices compared to striped cloth alone. The double-layer striped cloth treatment also improved safety, with a 130% increase in overwintering indices. Other treatments, including the soil-covered and the heat-insulating striped cloth, showed reduced performance. The sandwiched striped cloth and double-layer striped cloth treatments are recommended for northern China’s wine grape regions, with further research needed to evaluate their economic viability.