In this work we address the adequacy of two machine learning methods to tackle the problem of wind velocity estimation in the lowermost region of the atmosphere using on-board inertial drone data within an outdoor setting. We fed these data, and accompanying wind tower measurements, into a K-nearest neighbor (KNN) algorithm and a long short-term memory (LSTM) neural network to predict future windspeeds, by exploiting the stabilization response of two hovering drones in a wind field. Of the two approaches, we found that LSTM proved to be the most capable supervised learning model during more capricious wind conditions, and made competent windspeed predictions with an average root mean square error of 0.61 m·s−1 averaged across two drones, when trained on at least 20 min of flight data. During calmer conditions, a linear regression model demonstrated acceptable performance, but under more variable wind regimes the LSTM performed considerably better than the linear model, and generally comparable to more sophisticated methods. Our approach departs from other multi-rotor-based windspeed estimation schemes by circumventing the use of complex and specific dynamic models, to instead directly learn the relationship between drone attitude and fluctuating windspeeds. This exhibits utility in a range of otherwise prohibitive environments, like mountainous terrain or off-shore sites.