After being a regular starter for England on their route to fourth place at the World Cup in Russia this summer, Henderson is not due back at Melwood - the club's training base - until August 5.
However, the midfielder was keen to return sooner as Klopp wants all of his players to have had a full pre-season in the build up to their first game against the Hammers.
However, England teammate Trent Alexander-Arnold may be given permission to return early because of his limited role in the England side, plus the fact that fatigue is less of a concern due to his young age.
“It was a hard fight to convince him that he needed a holiday,” said Klopp.
“I knew it would happen. On the phone I said 'crazy'. Jordan needs a holiday so that means August 5 he will be back. Dejan [Lovren] had a party in Croatia and played a day later so he will be back on August 6. That would mean five days training after three weeks holiday.
“I hope we are in a situation where we don't need to think about using these two [against West Ham].
“With Trent I have a special agreement. He wanted to be in earlier as well. As he's very young I said, 'Okay, have two weeks holiday and then we'll speak and see'. If you asked Trent he would be good to join us in two weeks. But I'm not sure I will do that. I want to have them desperately but the season is really long. It will be difficult to involve them against West Ham but I don't want to make that line up today.”
Klopp was keen to dismiss suggestions that the England duo wanted to return early in fear of the fact that they could lose their places in the side to Fabinho and Nathaniel Clyne.
“That would mean they weren't confident and that makes no sense,” he said.
“Sometimes the manager has to say, ‘Stop! Make a break!’
“They shouldn't be worried about anything like that because we'll need them all. Trent was flying. He could probably play three years in a row but that wouldn't make sense.
Alisson— 90min (@90min_Football) July 18, 2018
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“I think three weeks holiday is really okay. Over the season we have days off. I don't want to sing a sad song but for players who play for their countries, three weeks in the summer is their holiday. Not too much but it's okay and they are used to it.
"In situations when we can do it, we give some time off. The Champions League starts again on September 18, until then they don't have games every three days.”