I broke my own rule about buying points — and saved thousands

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As a general rule, I always caution against buying points and miles without a specific, immediate use in mind. Airline and hotel loyalty programs can devalue their points without notice, and the last thing you want is to be sitting on a pile of purchased points that are suddenly worth less than you paid.

But for every rule, there’s an exception.

I recently found myself in a situation where buying points wasn’t just a good idea — it was a fantastic one, unlocking a stay at an ultra-luxe resort for a fraction of the cash price.

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I was scoping out a trip to the Conrad Koh Samui in Thailand, a truly aspirational Hilton property where even the base-level room is a one-bedroom tropical pool villa. Yes, you read that right: Every room has its own private pool.

The privilege of a private pool villa with stunning ocean views comes at a steep price. The cash rate for our dates was hovering around $1,431 per night. An award stay, meanwhile, cost a hefty 180,000 Hilton Honors points per night. I had a decent stash of Hilton points from regular spend on my Hilton Aspire American Express card, but not quite enough for the length of stay we wanted.

This is where the exception to the rule comes in. Hilton was running one of its frequent promotions offering a 90% bonus on purchased points. This allowed me to buy 304,000 Hilton points for just $1,600.

That changed the math completely. By using points that I had effectively purchased for $0.005 each, the real-world cost of the room dropped to just $900 per night (180,000 x $0.005). That’s a massive savings of $531 every single night compared to the cash rate.

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The deal got even sweeter. I combined the points I had just purchased with the points I already had in my account to reach a total of 720,000 points. That was enough to book four nights at the resort.

But here’s the final bonus: I have Hilton Diamond status, which I get automatically just by holding the Hilton Aspire card. One of the best perks of Hilton elite status (Silver and above) is the 5th Night Free on award stays. So, my 720,000 points didn’t just get me four nights — it got me five, further reducing the effective nightly cost and stretching the value of my points even more.

While buying points speculatively is a risky game, this is a perfect example of how it can be a real win when you have a specific, high-value redemption in mind. Always do the math, and you might find that buying points is your ticket to a luxury stay you thought was out of reach.

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