Background: Actinic keratoses (AK) usually occur on sun-exposed areas in elderly patients with Fitzpatrick I–II skin types. Dermatoscopy and ultrasonography are two non-invasive tools helpful in examining clinically suspicious lesions. This study presents the usefulness of image-processing algorithms in AK staging based on dermatoscopic and ultrasonographic images. Methods: In 54 patients treated at the Department of Dermatology of Poznan University of Medical Sciences, clinical, dermatoscopic, and ultrasound examinations were performed. The clinico-dermoscopic AK classification was based on three-point Zalaudek scale. The ultrasound images were recorded with DermaScan C, Cortex Technology device, 20 MHz. The dataset consisted of 162 image pairs. The developed algorithm includes automated segmentation of ultrasound data utilizing a CFPNet-M model followed by handcrafted feature extraction. The dermatoscopic image analysis includes both handcrafted and convolutional neural network features, which, combined with ultrasound descriptors, are used in support vector machine-based classification. The network models were trained on public datasets. The influence of each modality on the final classification was evaluated. Results: The most promising results were obtained for the dermatoscopic analysis with the use of neural network model (accuracy 81%) and its combination with ultrasound scans (accuracy 79%). Conclusions: The application of machine learning-based algorithms in dermatoscopic and ultrasound image analysis machine learning in the staging of AKs may be beneficial in clinical practice in terms of predicting the risk of progression. Further experiments are warranted, as incorporating more images is likely to improve classification accuracy of the system.