Bordatella vaccine is advised in any situation where multiple dogs are coming and going, and encountering each other in a relatively enclosed space - i.e. boarding kennel, groomer, etc.
From what you describe, his risk of being exposed to "kennel cough" is relatively low so it is up to you. He could still get it, even playing with a dog that maybe is not showing symptoms yet, but it's not likely so it's probably safe to skip it. It's not typically life-threatening (sometimes very young puppies or very old dogs end up with pneumonia) - just causes a hoarse cough that requires antibiotics to clear up. I tend to recommend certain vaccines based on the dog's lifestyle, exposure risk, and how serious of a disease it is if they do catch it.