Morgana, thanks for the response. I was hoping to hear from you.

What about if we stay in York itself for the first day or two of our trip, then move on?

Would Helmsley then still be a good choice for the next part of the trip?

We don't really want a busy or bustling town for this Moors and Dales part of the trip; we would prefer something "chocolate box" because that is much more exotic and exciting to us. We spend our days at home in a place that is fairly busy and bustling, so quiet and quaint seems attractive.

I've got a list of Helmsley cottages that will take us for 6 nights (although we may be paying for 7 and wouldn't know it) using a cottage listing website.

Thirsk is off the list, and I'm looking at Helmsley.

Silly me, thinking that just because I got listings when I plugged in my dates, that we could rent for less than a week. It doesn't look good, so I'm switching to B&Bs.

Hi
You can usually get a part week cottage out of season but you are visiting at a fairly busy time - school half term holiday and the Spring Bank Holiday. B&B would be fine though, and there are some lovely ones around.
I think staying at York and then in or around Helmsley would work well. Helmsley is popular partly because it is so pretty (and has its castle, proximity to Rievaulx etc etc) but I think you would like it.
www.ryedale.co.uk/ryedale/helmsley/helmsley.html
Carlton Lodge looks very nice.
http://carlton-lodge.com/
Thinking about pretty villages, much smaller than Helmsley but very attractive is Hovingham in the Howardian Hills. This is a really lovely village with church, stream running down the side, village green etc.
It has a small Hotel called the Worsley Arms and probably has lots of B&Bs too.
www.worsleyarms.co.uk
I've had a quick look and you may want to investigate these further -
www.no54.co.uk
www.westviewcottage.info/

Liverpool is most definitely worth it

I'm checking these out, Morgana. Thank you.

alihutch, can you recommend a place to stay in Liverpool? We are looking for maybe 100 £ or so. Less would be great.

cimbrone, I forgot to mention that I've printed your trip report and I'm using it in my planning. Thank you.