Tam, I agree that it is not going to be much of a holiday if you are worrying about the dog. But at the end of the day you know your dog best and what is best for him. I think you should go with your gut instinct and not over think it too much. Trust yourself and your ability to make good decisions about those you love.
What every one has said is obviously right - there are good kennels and bad kennels, there are pro and cons to leaving him at home and getting someone in, etc etc. As suggested do your homework as of this very second and make an informed decision. The advice you have been given on how to pick a good kennel is priceless - take note.
Whatever your decision is once you have made it try to remember that things can always go wrong (hate to rain on the parade but....). That is, unfortunately, life. Dogs can go to a kennel and get kennel cough and dogs can stay at home and then decide to dig their way out. You can only do your very, very best and then what the future holds is really out of your hands. But when making your decision think about the implications if something did go wrong - ie, kennel cough can (generally) be easily treated with antibiotics but digging out and being hit by a car obviously has more serious consequences.
Either way remember you can call your pet walker/sitter or the kennels and check on your pet everyday if you desire. This may give you peace of mind. OH can do the same.
Do have an alternative plan in case the one you go with crashes.
I am a fence sitter when it comes to home minding versus home based minding versus dog kennels. I believe all three are valuable businesses for pet owners to access. Not all dogs are suited to kennels, whilst some thrive in this environment, not all can go to someone elses home and be happy and some are just happy to stay in their own home whilst others hate it. I do believe though you get what you pay for with most dog minding services. My opinion is if you scrimp don't expect much. In saying that paying over inflated prices does not always guarantee a better service.
What really separates your options are your beliefs, your dogs personality and ability to adapt to new environments and what you are most comfortable with.
I take my dogs away with me as a rule but have left them on the odd occasion with clients, once they stayed home for two nights with a pet sitter visiting and once they were in kennels for three nights. I actually drove the dogs from Sydney to Dubbo and then placed them in kennels so if something happened I was close by. My point is regardless of where I leave my dogs I worry and fret - yet they always seem to be fine! and certainly not scarred by my choices.
I run a home based dog minding business. If you decide to pursue this option please make sure the place is secure, they want to meet you and your dog and they let you inspect the property, make sure they want things like an emergency contact number and your vet details, ensure they want to know your dogs food and exercise needs and whether he is afraid of storms, etc etc. Most of all watch how your dog responds to them - dogs never lie about their feelings towards people.
Good luck. I understand your worry and the fact that you are considering what is best for your dog shows you are a great pet owner who will make a great decision.