I get this.
Now it's our cat. But we board him with our cat only vet and it's wonderful. He takes medication everyday, so I know he's in great hands. They send us texts and pictures about twice a day, he has his own big room and they just love on him all day. I dread the days before we drop him off, always want to cancel, but once he's there and we are on our way we have a great trip knowing he's well taken care of. We board him 10 or 11 nights each time.
Try boarding your dog for a couple nights before you go, by the second day most pets are usually acclimated to where they are staying. This would give you a good idea of how he'll do and maybe make you feel better?
My advice would be don't read the internet, which of course is full of horror stories about pet boarding, especially cats! In reality, most pets do just fine. Do they love it? Probably not. Will they get over it once you are home? Absolutely! Don't miss out on vacations, they are important.
And if I'm this crazed about a cat, I don't know what I'd be like with a baby!