It's such a difficult decision to make isn't it?
We have always taken our dogs to 'pet-friendly' rental homes where possible, hotels for us seem to be a bit of a no-no with Harry as he makes a racket being left in a strange room...
There are times though when taking him is out of the question (for instance when Andy + I visit my son who lives in Vienna). I put an ad on the board at our Vet's, and placed an ad in our local newspaper. I interviewed masses of people, boiled it down to a few - and then went to check-out
their homes (as we too didn't want strangers coming into our house).
I've settled on 3 different people, just in case one was busy at the specific time I needed them...the ones that I've chosen only take 1 dog at a time (unless from the same family). Then I went about it gradually - leaving Harry for just a day from 10-5, then leaving him overnight for just one night etc. etc.
Well done you on starting the thought process early - it'll ruin your holiday if you're not completely confident with the care you've put in place
Good luck! Sally + Harry x