Reliable assessment of grapevine productivity is a destructive and time-consuming process. In addition, the mixed effects of grapevine water status and scion-rootstock interactions on grapevine productivity are not always linear. Despite the potential opportunity of applying remote sensing and machine learning techniques to predict plant traits, there are still limitations to previously studied techniques for vine productivity due to the complexity of the system not being adequately modeled. During the 2014 and 2015 growing seasons, hyperspectral reflectance spectra were collected using a handheld spectroradiometer in a vineyard designed to investigate the effects of irrigation level (0%, 50%, and 100%) and rootstocks (1103 Paulsen, 3309 Couderc, SO4 and Chambourcin) on vine productivity. To assess vine productivity, it is necessary to measure factors related to fruit ripeness and not just yield, as an over cropped vine may produce high-yield but poor-quality fruit. Therefore, yield, Total Soluble Solids (TSS), Titratable Acidity (TA) and the ratio TSS/TA (maturation index, IMAD) were measured. A total of 20 vegetation indices were calculated from hyperspectral data and used as input for predictive model calibration. Prediction performance of linear/nonlinear multiple regression methods and Weighted Regularized Extreme Learning Machine (WRELM) were compared with our newly developed WRELM-TanhRe. The developed method is based on two activation functions: hyperbolic tangent (Tanh) and rectified linear unit (ReLU). The results revealed that WRELM and WRELM-TanhRe outperformed the widely used multiple regression methods when model performance was tested with an independent validation dataset. WRELM-TanhRe produced the highest prediction accuracy for all the berry yield and quality parameters (R2 of 0.522–0.682 and RMSE of 2–15%), except for TA, which was predicted best with WRELM (R2 of 0.545 and RMSE of 6%). The results demonstrate the value of combining hyperspectral remote sensing and machine learning methods for improving of berry yield and quality prediction.