The aims of this study were to analyse the stress distribution developing around an orthodontic miniscrew (OM) inserted into the maxilla and to determine the stress field changes for different screw lengths and for different levels of osseointegration occurring at the bone/screw interface. An integrated experimental/numerical approach was adopted. Using the photoelastic technique, the stress field arising in the bone after screw insertion and the application of the initial orthodontic load was assessed. The finite element (FE) method was used to determine the stress acting in the bony tissue after a given time following screw application, when, for the viscoelastic relaxation effects, the only stress field remaining was that due to the application of the orthodontic load. Different levels of osseointegration were hypothesized. Photoelastic analyses showed that stress distribution does not change significantly for moderate initial orthodontic loads. From the FE simulations, it was found that critical conditions occur for screws 14 mm long with an orthodontic load of 2 N. The optimal screw length seems to be 9 mm. For such a dimension, small stress values were found as well as low risk of lesion to the anatomical structures.