Short stay in Liverpool/Wales

I took the Holyhead-Dun Laoghire ferry in a February and swore I would never do it again. The weather was actually fine, it just takes so long and the ships are not very comfortable. Now granted, I started the day in London and had the rail journey to Holyhead as well so it was an extra-long day, but I would still recommend flying.

Although I did enjoy seeing the North Wales coast, I would not bother with it in winter.

I like the idea of staying in Chester. It looks lovely. Any idea of a hotel that would allow 5 guests? I do find some apartments... is the city rather easy to get around if we stay somewhere close to the cathedral?
In this case, we could spend 2-3 nights and take the 10:00 pm flight to Dublin. This would give us 11/16- arrive, eat and crash, 11/17 for Chester/Liverpool, 11/18- free to explore Wales, 11/19 Liverpool and flight out. Does that sound reasonable or should I really add a night? Given that Wales will likely be bleak, would Conwy maybe be a good choice? We would at least like to get a glimpse at the Welsh culture, no matter how short.

Thanks for your super helpful replies! We used to book a room for 4 and just sneak in with the 5 of us, but with the kids being older now, it isn't usually a good idea. I checked on Airnb and there are a couple of reasonable apartments either on Tower Road/New Crane or on Hoole Lane. Some hotels are reasonably priced enough for us to consider two rooms. They are on city road, Little St. John and Lower Bridge Street.
Are any of these areas better than another?
I guess the "Welsh culture" I refer to really is the language and history. We apparently have a lot of Welsh in our own heritage, so it would be kind of cool to see the castles of our ancestors. Plus, the language is super interesting to my kids.
I will definitely consider staying an extra night as you suggest, though the flights out the following day are quite a bit more expensive for some reason. If we spent, 1 day in Wales, 1 day in Chester and then, the last day in Liverpool (flight leaving at 10 pm), maybe we could store our luggage at the train station that last day and still get to Dublin that night. Sounds kind of exhausting, but most vacations I plan end up that way no matter.

Thanks. I was looking at the Quarterz Hotel on City Road, or the Travelodge Chester Centre on Little St. John Street as decently priced hotel options. We would probably be okay with the college area but, it will be a weekend so, your advice on the noise may be something to consider.
I think based on what you have said, I would rather be closer to the city centre than the station. Although, a 10 minute walk is certainly not an issue.
They would enjoy the signs and certainly, would love to hear the language spoken. Is it fair to say that anywhere in Wales we will find that? Of course, I understand that we won't have Welsh spoken to us necessarily as tourists. I will look into a tour from Chester although, we aren't really the "tour bus" types. I don't really like being hemmed in. We could also consider taking the train rather than driving as I read that it is a beautiful ride... any thoughts on that aspect?

I can’t help but wonder how you sneak a 5th “person” into a 4 person hotel room. If No. 5 is a small child or a very short adult, do you scrunch him down into a satchel? Or maybe you wait until the front desk is really, really busy, and scurry by with No. 5. Inquiring minds, etc.

Important notice: I don’t ever use emojis, so before reporting this post to the web master, be aware that this is meant to be humourous.

Sneaking the 5th person in wasn't really sneaking I suppose. We would just book as 4, one person would check in and then, the rest of us would find our way up to the room a bit later. It was really just a necessary thing to do if we were going to travel happily with all the kids being young enough to sleep on a couch or 3 to a bed.
We have similar Travelodge hotels in the States. Not sure they are the same, but I get the "modest" accommodations. That will work for us since we don't spend a lot of time in the room. I will call to see if they can bring in an extra bed.
If we train to Conwy, we won't really need a car, so, if we do rent one to tour around a bit I will schedule to return it the same day to avoid parking.
My husband is keen on seeing Caerfarnon Castle as he jokingly lays claim to it, being a great-great-great (etc...) grandson of Madog ap Llywelyn. So, maybe if we started out early enough we could get a taxi over that direction from Conwy... Or, maybe I can just distract him with Conwy Castle...LOL
((More inland, the Clywyd hills and countryside are pretty.))-- will take a look at that option online as well, thank you!
We will keep our ears open for the language!

Note taken on the rooms! I will book two separately or just get an apartment if need be.
That is funny about the heritage! I actually spent a lot of time on both of our family trees and Gruffydd ap Llewelyn came up in both mine and his. Of course, I am not a scholar in this area, so it is very possible that there is an error in the tree leading to him. But, it is uncanny that he came up in both of ours. We got a good chuckle out of being "distant relatives".
Which of the castles do you think is most rewarding for a visit? Strangely, my kids aren't big on castles, having seen a few, but I still love them! Anyway, whichever has the most interesting township around it is likely the way we should go. If you have any recommendations for good pubs/restaurants and other things in Chester or Liverpool, I will gladly put them on my list.
We are huge Beatles fans, so definitely figure on visiting some of those sites... though not sure about the museum...

@Emma... what do you think of the location of this place? http://www.riverdeeholidayhome.co.uk/ It is pretty reasonable in price and looks lovely with parking.....

Super! My kids are older teens, so the river and the walking is not a concern. I love the idea of being on the river and relaxing there while I wait for my slow kids to get ready in the morning.

If you wish to find bus times in Wales - use >https://www.traveline.cymru

For train times & fares > www.nationalrail.co.uk
I have just checked for a return ticket (pay at Chester station) for Chester to Bangor = £29.80 per adult if you catch the 9.58am or earlier (on weekdays). However, for the 10.16 (arrives Bangor at 11.24) or later, the price drops to £18.70 return. (You would need to check the schedules nearer your date of travel). For longer trips - such as Chester to London - you will find the cheapest Advance fares (for specific trains) about 11 weeks ahead. If you went to Caernarfon Castle first, you could then return to Conway (Conwy) but if you do this - make sure that the train stops at Conwy. (Virgin trains don’t but most Arriva Trains Wales services do BUT you must inform the guard on leaving Bangor that you wish to get off at Conwy. When you leave Conwy - hold your hand out as the train approaches as it is a request stop).

This map shows you the percentage of people who speak Welsh in different areas. As you can see, it varies widely from practically nobody in parts of the east up to around 90% in the more sparsely populated west.https://www.google.co.uk/search?q=map+showing+percentage+of+people+who+speak+welsh&tbm=isch&tbo=u&source=univ&sa=X&ved=0ahUKEwj46MPuiPjaAhUBOsAKHWP-ClMQsAQIWA&biw=1702&bih=989#imgrc=aokfB4iEejSGPM:

Don't forget that both Conwy & Caernarfon Castles were built by the English King Edward I when he conquered Wales back in the 1200’s - so although they are in Wales - they are not actually castles built by the Welsh. Around 20% of the people of Wales speak Welsh and you will certainly hear it in Caernarfon.

Thank you very much! I couldn't find train ticket prices so far in advance. Did you just check earlier dates or, am I missing something?

That is correct - the cheap Advance tickets for November are not yet loaded - and won’t be for quite some time. When you go on www.nationalrail.co.uk and go to the calendar - advance it and you will see a grey background for those dates that currently have the cheaper advance tickets (for specific trains) loaded to the system. Right now (10 May), the cheaper tickets are loaded up to around 1 August. So, as time progresses, you will find that the price gradually rises for these Advance tickets - but even the day before, you can still get tickets for less than on the day. If you play around with the system and put in for your journeys - without actually making a booking - you will see how the prices change. Remember, you only really need to pre-book for the longer trips as the shorter trips stay at the same price. (It looks like Chester to Bangor falls into this category - so buy on the day but note that some services might be dearer than others).

When you make your booking, it will switch you through to the train company on which most of the journey will be made.

Thank you all! Last look at places to stay in Chester.... was going to go with Rondeva but, this place is about $50 cheaper per night, which would be helpful... Any Thoughts on location? Seems to be an alright place in general.
Approved Serviced Apartments Steam Mill, Chester3.5-star
Granary Wharf Steam Mill St., Chester, England, CH3 5BE, United Kingdom
Comfortable apartment with kitchen, near Chester Cathedral