Dublin - Hilton Properties, plus two or three nights?

We stayed at the Conrad in June 2012 on points and loved it. The room was nice, breakfast buffet (which was included) was excellent and we loved the location. It was a nice walk to St. Stephen's Green where we picked up the Hop-on-hop-off bus to tour the city. We bought the two day pass and were able to go anywhere we wanted in the city. There were many nice restaurants in the area. We found it very convenient to all we wanted to see. Highly recommend this hotel.

Have been in October, November and December and other than rain or some days being a little raw, was not that bad. In Dublin would skip Guinness brewery, felt it was too expensive and on a cloudy day can't see much from rooftop bar. Highlight was Christchurch cathedral. Book of Kells and my all time favorite is Kilmainhaim Gaol. Went there once in late November and have never been so bone cold. You start off in a chapel where one of the rebels married his fiancée just before he was executed. The guide told us to take off all of our outer clothing, coats, sweater, etc. while she gave presentation, reason being so that once we went inside to the cells with our coats on, we would feel warmer. We thought she was crazy but did as she asked and were we glad. Been there other times, but this was cold. Only problem with December if going to places such as Dingle, some B&Bs will already be closed and not sure what you can see without car. Also just curious, why are you starting in Kinsale and how do you plan to get there and then from there to Dingle. Although we love Dingle, from Kinsale it will be by bus and once in town there is not that much to see for two days, just my thoughts. If you give us more information, maybe some others can be more helpful.

I left out a few details. We are flying into Dublin on a Tuesday, where we are renting a car and driving towards Kinsale. We have a place in Kinsale for three nights (Thursday, Friday, and Saturday). Which means we are still looking for a place to stay halfway between Dublin and Kinsale. Any ideas?
After our visit to Kinsale, we will drive to Dingle for two nights. Then we have four nights until we depart Ireland.
We were originally going to stay two nights in the Galway area and then two nights in Dublin (one being New Years Eve). However, I'm leaning towards one night on the way to Dublin, then three nights in Dublin. Any thoughts or ideas on a route to Dublin?

We will drop car at airport when we arrive in Dublin and that's where we will go by bus, taxi, or train.
Thanks everyone!

You can drive from Dublin to Kinsale in about 4 hours, or you can stay overnight at Cashel (not at a Hilton), to see the Rock of Cashel fortification and cathedral.