Italy Sep 20th,1st stop, Bologna- then I take the train to Riomaggiore or Monterosso villages in Cinque Terra. Problem is finding a place to spend the night of Sept 21st. Any village along this stretch of the coast will do, I've been on the web and only have bad luck with all the typical hotel web sites, then I discovered that there is a rental office in Riomaggiore that will rent a room in a local home.?.Is there any one out there with more experience with this style of stay in Italy?
Is it worth the "Risk" of chancing I'll get a place for the night?

Kealai,
Try http://www.wel.it/Welcome/Liguria/Cinqueterre/Riomaggiore/Alberghi/Vesigna/index.uk.html .
It's been about three years but I was happy with the rooms (2 couples) I booked in Riomaggiore. Pack light, for views you have to climb stairs.

Try www.5terre.com also. They were a good source for me.

I have clients staying in the CT on September 29...and I had a devil of a time finding rooms for them in Monterosso and Vernazza. To tell you the truth, I was surprised that so many hotels were filled mid-week in the last week of September.

You may have no problem snagging a room at the last minute, but just be aware, there are a lot of people in the area at that time.