We went the last 2 weeks of october last year, and it was lovely. The days were warm enough for the beach, and at night we just put on a jacket. Most of the restaurants have huge heaters that you really don't want to sit too close to, and Charlie's has a real fire. We had some rain, but we spent many a happy hour chatting to bar and restaurant staff who are usually too busy to sit and chat for long. By the last week, a lot of the restaurants and bars had closed, but there were still enough open that we didn't have a problem finding somewhere to eat or drink. There was a problem with hot water, but we eventually got the receptionist in the apartments to switch the boiler on in the late afternoon if it hadn't been very hot. It took some persuading, but he did it. Personally, I enjoy it when it's quieter, but each to their own. If you're the kind who wants 24 hr entertainment,
Icmeler in late october isn't the place to be.