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I missed out on a free hotel night — reader mistake story

Oct. 14, 2019
4 min read
Jamaica_David Neil Madden_3
I missed out on a free hotel night — reader mistake story
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Today, I want to share a story from TPG reader Aaron, who booked the wrong room type to take advantage of a Hilton Honors elite benefit:

My wife and I booked a mini-moon to Jamaica, I booked our flights with Delta miles, and figured I'd make the most of my Hilton points on a five-night, all-inclusive stay in Montego Bay. I was happy that the entire trip was going to cost me 60,000 SkyMiles, $200 in fees and around 240,000 Hilton Honors points (getting the fifth night free).

I had never used the fifth-night-free benefit, so I called Hilton to ensure that the resort we chose qualified (it did) and to book our stay. I booked the trip, and thought nothing additionally of it. Unfortunately, I didn't read the fine print for getting the fifth night free, which apparently only applies to "standard rooms." After the trip, I looked at the receipt and realized I was charged almost 300,000 points, and that the fifth night wasn't covered.

I went back and forth with Hilton customer support and acknowledged my mistake, but was essentially told "you should have read the fine print." I'm out roughly an extra 60,000 points for my trip, but it was a great getaway immediately after the wedding!

Yes, Aaron should have read the fine print, but I think the more fundamental mistake is failing to review his reservation. I recommend you always examine confirmation emails and receipts after booking. This protects you not only from your own blunders (like misunderstanding rates and loyalty program rules or inputting the wrong names and dates), but also from errors made by a booking agent or other mishaps like your airfare never being ticketed. If anything is amiss in your reservation, you're better off catching it right away — the more time you have to set mistakes right, the less you'll suffer for them.

As for that fine print, the Hilton Honors program rules state that the fifth-night-free benefit applies to Standard Room Reward stays only. You won't get a free night when booking a premium-room award, while stays booked with Points & Money or as part of a special offer or package are also ineligible. Finally, keep in mind that the fifth night free is only available to members with Hilton Honors elite status; just having an account isn't enough. You should be charged zero points for the fifth night on an eligible award, so if the numbers in your confirmation email don't add up, that may be a clue the benefit wasn't applied.

Related: Maximizing redemptions with Hilton Honors

I appreciate this story, and I hope it can help other readers avoid making the same mistake. In appreciation for sharing this experience (and for allowing us to post it online), I’m sending Aaron a gift card to enjoy on future travels, and I'd like to do the same for you. Please email your own travel mistake stories to, and put "Reader Mistake Story" in the subject line. Tell us how things went wrong, and (where applicable) how you made them right. Offer any wisdom you gained from the experience, and explain what the rest of us can do to avoid the same pitfalls.

Feel free to also submit your best travel success stories. If your story is published in either case, I’ll send you a gift to jump-start your next adventure. Due to the volume of submissions, we can't respond to each story individually, but we'll be in touch if yours is selected. I look forward to hearing from you, and until then, I wish you a safe and mistake-free journey!