McLaren are enduring their worst ever season, ninth out of 10 teams and without a win since 2012, while Hamilton has enjoyed another dominant year with 10 wins and his third championship.
Dennis, speaking at a marketing event in London last week without realising the media were present, voiced disapproval of some aspects of Hamilton's behaviour since he departed in 2012.
The driver has put much of his life on social media, enjoying the trappings of success and the party lifestyle that comes with it.
"If he was at McLaren he wouldn’t be behaving the way he is because he wouldn’t be allowed to...he's shaking off some chains he didn’t want to have," said Dennis.
Hamilton, whose jet-setting lifestyle has made the 30-year-old a regular in glossy magazines and celebrity websites, was bemused when asked about the comments at the season-ending Abu Dhabi Grand Prix.
"Why he is talking about me, I don't know," said the driver. "Maybe they don't have too many other positive things to talk about.
"Ultimately, that's probably why I'm here and a three times world champion. Who I am today is who I am and I would behave this way regardless of who I was working for. I don't feel like I behave wrongly.
"Just because I do other things outside of the sport I don't think it's a negative, it's obviously been a positive impact on my career," added the driver, who won his first title for McLaren in 2008.
"Maybe it's not me that needs to do any changes."
Hamilton was backed by both McLaren and Mercedes, then the team's engine partners, from his early teens and has spoken often about the huge debt he owes to Dennis and the manufacturer.
Dennis, clarifying his remarks to reporters in Abu Dhabi, also emphasised the high regard he had for Hamilton.
"None of what I said was anything other than positive," he said. "Lewis is unique, Lewis is living the way he currently wants his life to be...I'm fond of Lewis.
"If he was in the team I'm sure he would feel constrained and I'm sure he feels very free at the moment. It's not for me to judge which is the right way.
"I just feel there are ways you do things in McLaren and there's things that you do inside McLaren that are or are not acceptable. Some of those things (that Hamilton does) are at best on the edge.
"I hate Tweeting and all the other social media. I think it's not the way for the future."
(Reporting by Alan Baldwin, editing by Patrick Johnston)
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