Richard Brown was himself left disappointed by the news Thomas Cook had collapsed on Monday as he was due to shortly take his family to Florida.
He said: "We're in the same boat - we were due to fly out to Florida in a week's time - holiday of a lifetime sort of thing.
"It's just a sad, sad situation.
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"I was on a bit of a downer after the news broke and I thought if I could offer a few families a holiday it might cheer a few people up."
Richard had spent £8,000 on the trip to Florida and he now faces a long wait to get his money back.
"We can't just buy another £8,000 holiday - and when you go on the other travel agents they've put their prices up.
"Everyone is cashing in."
Since announcing his generous offer on Facebook, Richard has received over 500 messages from families who have lost out on upcoming holidays although he is primarily focusing on those who were due to set off in the coming days and weeks.
He continued: "We've got vacancies throughout September and October as the season is over and of the 130 caravans on site I own two of them so I'm going to be putting as many people as I can in them.
"There's a lot of upset people out there, if I can give them a couple of days that's better than nothing. I can't guarantee the weather and they might not be lying out on sun loungers but it's quality time with the family which is what holidays are all about."
The first family to stay in the caravans messaged Richard to say "We have just arrived, the kids were over the moon. Thank you so so much.
"Your caravan is beautiful the first thing I said was we’re definitely booking here next time. You have no idea just what you have done for our family, your kind gesture has completely flipped a horrific week over and made it much brighter xx"
On Facebook Richard wrote: "Hello everyone I am literally trying to prioritise your messages, if you should be away now or in the next few days and are available now this minute with your packed bags to get yourself over to Filey please inbox me ASAP.
"All you need to do is take your own linen and should you want to use Havens facilities then you will need to purchase their passes. Please inbox me ASAP as I am ready to allocate another 2 caravans."