I've done this a few times over the years. It can work out very well with the right person, in my experience someone who is more of a genuine companion. I've done it with both conventional WGs (in all those cases sourced through the KLE collective) but more recently Seeking has been the much better option for this. Be alert, though, that even with very careful preparation things can turn out badly: I've experienced that too.
In all cases it's something I have only broached with the girl after we have built up a very good rapport over a fair few shorter meetings, establishing as much common ground as possible on interests, conversation topics, food preferences etc etc. The key to success is realising that going away on a trip of this kind is more like going on holiday with a partner than with an escort/SB - it's not non-stop sex!
It's very important to have very well established ground rules - eg on spending time apart, frequent of sex etc etc (though my experience is that the SB route offers more flexibility in general).
Cost wise, it's certainly not a cheap option. You'd normally have to expect to pick up all travel and accommodation costs as well as food, drink, activities etc. On top of which the girl will require 'compensation' for her time. Good escorts will have established rates for this kind of thing and they can run well into the £000s for a week. SBs offer more flexibility and I have done trips where they range from just wanting a free holiday, so no additional cost, to £000s comparable to a high end escort.
For this kind of thing to work well requires a huge investment of time and effort (and money) and you really need to be very confident that whoever you choose to go with approaches it in a similar spirit. If it goes wrong (and it can very, very very easily!) it becomes a very costly error and one that you regret for a long time afterwards.
