Unfortunately you have opened the can of worms that is cyclopropylmethyl carbocations.
It is known that the parent unsubstituted cyclopropylmethyl carbocation is non-classical, and leads to mixtures of cyclopropylmethyl, cyclobutyl, and homoallyl derivatives. However, the presence of substitution can alter the electronic structure quite significantly. There is too much on the topic to discuss here; the interested reader may find reviews for themselves in George Olah's books Onium Ions and Carbonium Ions.
In this case, I would say that it is virtually impossible to predict which major product will be formed. Perhaps that's not the answer you wanted, but I don't want to propagate fake knowledge and claim that we can predict something that we can't.
Looking up this reaction on Reaxys, I find that it has not been done before. However, the reaction of the corresponding alcohol with HBr has been reported before. In different people's hands and under different conditions, it gives different major products; both the cyclopropylmethyl bromide and the homoallyl bromide have been isolated. [Apparently not the cyclobutyl bromide, though; why? Again I don't have a good answer.]