I think it's probably been 20 years since DH didn't work on holidays.
I do all the planning and organising. The night before the trip he will finally do his own packing, after asking me what the weather will be like where we are going. He will work late the night before leaving, work early on the day of leaving and will have his laptop out in the airport lounge.
We travel a lot, so it's sort of a compromise really. I've had a job with good holidays and leave, he's self employed, so no sick leave or holiday pay. I also realise that working makes him happy. He will participate happily once we are away, but I make sure I try to plan days so he can easily work for some of the day. If we do a full day trip sightseeing, I let him know in advance, so he can try not to schedule meetings on that day.
It's not that I don't get frustrated sometimes, when I'm enjoying the view and he's got his head in the laptop, but, it helps make the money for the next holiday/
On our last trip, I booked one bedroom apartments in a number of cities, this meant DH could get up early and work in the lounge and let me sleep. He would work from 6-9am, then we would go to breakfast together. After breakfast, I'd go out alone for 3-4 hours, letting him work. By 1pm, I'd go back and get him and we would spend the afternoon exploring together. We'd have a late afternoon rest and sometimes he would work while I rested, then we would be out for dinner and more sightseeing. We head overseas again in a few weeks and will do almost the same thing.
When we cruise, I like to read in the sun, he burns easily, so that's his work time, plus early morning. He will go and get coffee and take his laptop. He's never alone, there's always quite a group of people working on each trip.
I think if your DH is always going to work, then you might as well just plan it in your day. That's a whole lot better than staying home.