Don't put human emotions on dogs they will be fine. They live in the moment and as along as they are not stressed, cold, ill or hungry etc they will be fine.
A big con for a kennel is that usually assuming it is a good boarding kennel, the dog will be safe.
Left with a house sitter they can run off, get into all sorts of problems. But having said that a good house sitter may also water your tomatoes and spoil your dog rotten.
Putting a young dog into kennels is a great way to get them used to it. I would leave him for one night and see how he gets on. They do not miss people like we do and if they have food, are warm and dry and have entertainment like barking at other dogs what more could they need for a short while.
I usually take our dogs with us so have been holidaying in europe and this country but that is because I like doing doggy things on my holidays - long walks, agility etc.
However we have left them in kennels when we went to Australia and also left them with a home sitter as well. I felt happier with them in the kennels.
If you really want a doggy holiday caravan and this country is the way forward! Never mind about the wrecked image!