We are going to be in Italy (Rome, Sicily, Sardinia, Genoa, and Milan) for the whole month of September and had no problem finding reasonably priced places to stay--we did all the bookings around the third week of July. I generally use Booking.com and Airbnb to find places--we are happy with pensiones and Airbnbs and prefer them to big hotels. I find that Booking.com's customer rating system is very dependable--anything over an 8.5 rating is a fine place to stay, and many of our places are in the 9+ range. I think we're paying in the neighborhood of EUR 95-115/night in Rome, Genoa, and Milan. Sicily and Sardinia will be cheaper, averaging maybe EUR 75/night.