Can I achieve this with widgets? Or do I need custom coding - can pay for help.

I'm in the process of moving my site over to wordpress (using Atahualpha of course!). It currently resides half completed here.

My problem/query is best explained by looking at this page.

It describes one of the holidays. If you scroll down a little, on the right you will see a couple of widgets, one for main hotel and another for alternatives (upgrades/downgrades). Holidays will have different hotels available, though some holidays share the same ones. An added complication is that I also want to show (for some holidays) hotels for outward/return trips as it can take a couple of days to reach the holiday destination by train.

Currently, each holiday and hotel is a separate post and I've tried creating links, via tags, to show related posts in the widgets (and used widget logic to show only certain ones on certain holiday posts) but cannot get it to work correctly.

Also, as I have some 25 holidays and 60+ hotels, each one will need different hotels showing on different holidays, so even if I could do it with widgets I'll need a lot of them in the sidebar to cover all hotels. So could I do this with just 3 widgets (main, alternative and en-route hotels) that would show the correct hotels for the currently being viewed holiday post or is that beyond wordpress as it comes out of the box?

Should I make the hotels static pages instead or change the categories I use (all hotels are in one category now - should I have sub cats for hotels in the relevant city?)?

I'd be prepared to pay for some guidance on this as I'm tearing my hair out trying to figure it out.

Hope this is clear, but if it needs further explanation please get in touch or post here.

Thanks for ANY help on this.
Nick