Timing a trip

Probably, but I have not seen that big a difference between with hotel that have a prime location. It will be cheap that peak but 50%. But you do stand a better chance with cheaper walk up rates if prepared to do a little looking.

in general, Yes. Coming off of high season most hotels should have some reduced rates though some may not be drastic reductions as much of Italy has become a year round destination. Many hotels have websites that will show the range of rates depending on the seasons.

It depends where you are. In the Dolomites, we saw prices drop around 26 August when the kids go back to school. In Venice, it seems high season continues through October and prices to not drop until November. In Florence and Rome they may not drop at all. Places that are specifically geared toward summer vacation activities---beaches and mountains---are more likely to have a "low season" beginning sometime in the autumn than the big cities, which attract tourists year round.

In Rome in October our RS recommended hotel said October was a high season month due to the good weather. The desk clerk stated they drop their prices for January- March!
In Milan the hotel prices are more dependent upon the convention schedule.

Lola is spot on. It depends on where in Italy.

we got discounts in CT (Monterosso) in early October. Everywhere else--Rome, Florence, Venice--betwn sept 28 and Oct. 18, was not discounted. We lucked out. weather in CT was gorgeous for our 4 days there.