Hilton’s funny math: save points by extending a stay


I’m about the closest thing you’ll find to a Hilton fanboy in the blogosphere, but Hilton’s award pricing vexes and perplexes me at times. I’ve previously showed that their program is reasonably rewarding (Greg’s take was a bit different than mine) and then Greg ran the math on how Hilton’s not even a bad deal in terms of manufacturing free nights in some instances. However, I wrote a post a year ago about Hilton’s poor math skills when it comes to pricing award nights. Unfortunately (/ fortunately ?), their math has not improved. That means it is a pain to make sure you’re getting the best deal for an award stay — but it does create windows of opportunity in that you can sometimes save points by booking a longer stay.

a bed in a room

In last year’s post (See: Hilton stinks at math: book award nights separately), I showed that rather than averaging the cost of award nights on a multi-night stay, Hilton sometimes priced all nights at a higher award level when you book a multi-night stay. I gave one example where a 5-night stay would cost a boatload more points than booking 5 individual 1-night stays. Due to Hilton’s revenue-based award pricing, my end-recommendation was to search and book nights one at a time to get the best deal. See that post for more detail.

Recently, I ran into the Hilton computer oddly pricing rooms the opposite way — cheaper on longer stays. In fact, while Hilton’s 5th night free clearly should drop your per-night average cost down, I also found that 5-night award stays can often cost fewer total points than 4-night stays, prompting me to take a closer look at my award reservations.

Five separate nights

Take the Doubletree Omaha Downtown as an example (Note: I was not reserving this hotel, I just pulled this up randomly for an example here). I looked up nights individually from October 10th, 2018 to October 15, 2018. If you look up each night separately as 1-night stays, here is how this hotel prices out for a standard room (2 Queen Beds Non-Smoking):

  • October 10, 2018: 33,000 points
  • October 11, 2018: 26,000 points
  • October 12, 2018: 26,000 points
  • October 13, 2018: 36,000 points
  • October 14, 2018: 33,000 points

If you were to book those five nights separately, your total cost for 5 nights would be 154,000 Hilton points.

Dynamic pricing for different lengths of stay

When you start entering those dates in various multi-night combinations, award pricing is dynamic. For example, here is a 2-night stay from October 12-14, 2018:

a screenshot of a computer

As you can see, the cost of October 12th has now increased by 10,000 points. I find it interesting that a 2-night stay costs more than two one-night stays as the hotel presumably incurs slightly less cost in not having to completely turn over your room after Day 1, but I think it’s fairly common for hotels to price this way (perhaps you get overcharged for the convenience of having your stay booked together as one contiguous series of nights)..

Not surprisingly, expanding the search to a 4-night stay dropped the nightly price a bit as compared to the 2-night stay, coming in at 33,000 points per night.

a screenshot of a computer

However, falling in line with last year’s post, you would still be better off booking those 4 nights separately. If you go back up to the individual night prices I listed above, you’ll note that October 10-14th add up to a total of 121,000 points if booked as separate 1-night stays (33K + 26K + 26K + 36K) versus paying 132,000 points for a 4-night stay. You’d save 11,000 points by booking your nights individually (and I’ve personally never had difficulty getting a  property to later string those together so that I could keep the same room during my stay). So far, the info above fits into what I outlined in the previous post a year ago.

However, I recently discovered that it can get interesting when you add a 5th night to the mix. Here is October 10th-15th, 2018 priced out when not logged in to Hilton.com as an Honors member:

a screenshot of a computer

Interestingly, you’ll note that unlike in the previous examples where all nights priced the same (all 36K or all 33K), the 5-night stay prices the nights individually in the breakdown. And it prices them cheaper than if booked separately — to the tune of 10K total points fewer than booking nights separately (144K points for 5 nights booked together versus 154K points for 5 nights booked separately). This makes some sense to me as I’d expect the hotel to want to offer some incentive to book a longer stay (which presumably brings them more income and costs them less to offer).

Five-night stays can lead to total savings (not just average per-night savings)

But here’s what I found interesting: Hilton Honors members get the 5th night free on award stays and Hilton is charging differently than I would have expected in that case. I would have actually expected the 5th night free to be based on Hilton’s 4-night pricing: 33K each night with the 5th night zeroed out. However, Hilton instead based the price on 5-night pricing and zeroed out the 5 night.

a screenshot of a computer

Oddly enough the result is that a five-night stay can cost fewer points than a four-night stay. That’s not fewer points per night, which one would expect due to the 5th night being free, but fewer total points. As you can see above, a 5-night stay costs 115,000 points, whereas a 4-night stay would have been 132,000 points (if booked under a single reservation) — a savings of 17,000 points by booking a 5-night stay rather than a 4-night stay!

Side note: If you were to take advantage of the current point transfer bonus from Membership Rewards to Hilton, the 5-night stay above would cost you 45,000 Membership Rewards points (45K x 2.6). While I probably wouldn’t make that transfer myself, the cash rate for the same dates comes to $666 — yielding a 1.48 cents-per-point value. That’s not too far from the 1.5cpp value of Ultimate Rewards when booking travel via the Chase portal with the Sapphire Reserve card…and this one doesn’t require you to carry a $450/yr card. Again, this wouldn’t be my preferred use of Membership Rewards points, but it’s an example showing that they can be used for reasonable value against hotel stays.

For those curious, I found Hilton’s flexible date search to be pretty useless. For example, here were the results for flexible dates on a 5-night stay:

a screenshot of a hotel schedule

As you can see, the dates used for the examples above (October 10-15, highlighted in yellow) show they are available “from 30,000” points. Five nights at 30K would be 150K points — which isn’t a total you see in any of the examples above. That’s because when the room rate changes during a stay, Hilton only displays the rate for the first night, regardless of whether it’s the cheapest or most expensive night. The flexible date search will only tell you the price of the night you’re checking in — you’ll have to look at the detailed breakdown to figure out how much they are charging for each night.

Back to Hilton’s 5-night pricing, the point-savings and/or value proposition can be quite significant in some instances. In fact, the situation that drove me to this post was a hotel where a weekend stay was ringing in at 89K points per night for Friday and Saturday nights (178K total for 2 nights). I was actually going to be in town for 4 nights, but thought I would likely spend the first two at another property and then move to the 89K property on the weekend using free weekend night certificates from our Hilton Honors Aspire cards. We figured we’d get pretty good value out of the certificates by using them to save 89K points each night (and when room rates with tax were well over $400 per night).

a screenshot of a graph

When I looked up a 4-night stay at that property, the price came down to 75K each night for a total of 300K points.

a screenshot of a cell phone

I then remembered that the 5th night would be free on an award stay, so I thought it might make more sense to save our weekend night certificates and book a 5-night stay. I figured the cost would still be 300K points, dropping our average cost-per-night to 60K, which was reasonable enough to me (and we had the flexibility to stay for a 5th night). To my surprise, a 5-night stay came down to a total of 280K points.

a screenshot of a cell phone

Staying an extra day not only dropped the average cost per night over five nights down to 56K, but it saved 20,000 total points over staying four nights. I expected the former, but not the latter. Needless to say, I decided that a 5-nght stay for 280K made more sense than using two weekend night certificates plus two nights elsewhere. It’s worth noting that a 3-night stay at this property during my dates would have been 267,000 points (89K x 3).Thirteen thousand additional points for two more nights is a pretty solid deal.

Of course, this plays right into Hilton’s hands in terms of breakage — will I still use my free weekend certificates to good value? Thankfully, I have a plan for those still.

Bottom line

Hilton is obviously very different from Marriott, Hyatt, IHG, and other competitors in that the Hilton award system is revenue-based. While dynamic award pricing can be a negative in the sense that it is difficult to get outsized value out of your points, it can open up opportunities for point savings in some cases. While I’d expected that a 5th night free booking would drop the cost per night, I found a number of instances where it also dropped the total cost — meaning that even if you only intend to stay for four nights, it might be cheaper to book 5. That won’t work in every situation since Hilton is so dynamic and unpredictable, but it’s worth looking at your award stays to see if they may price cheaper by adding nights.

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I made a reservation with Hilton Reservations for the Hilton in Belgrade, Serbia for fourteen nights at a rate of EU 122.50, and then made a reservation for another room for the first five nights of the first reservation, and was shown a rate of EU 109. Curious, I checked the rate for the nights after the first five, and found it was EU 122.50. It appears that Hilton books an entire reservation at the highest rate in effect during the stay instead of booking the stay for a day by day rate at the rates in effect for each day. I called Hilton reservations to inform them of this, and they cordially adjusted the rates. While they made the adjustment cheerfully by making two separate reservations for me, I find this pricing practice unfair and deceptive. Had I not checked other days for a second room, I never would have known of the existence of the lower rate for those days.

[…] is to search nights both as a 5-night stay and individually to be sure you get the best deal. See: Hilton’s funny math: save points by extending a stay and Hilton stinks at math: book award nights separately for more on this […]

[…] right direction as to the best deals, but unfortunately neither will give you the full story. Like Hilton’s funny math, these tools are highly […]

[…] month, I wrote about the phenomenon of Hilton’s dynamic pricing stacked with its fifth-night-free for Hilton Honors members causing some 5-night stays to cost less […]

[…] Miler gives details about an upcoming Hilton stay using Hilton Honors points. As it turned out, it was less points for him to stay five nights instead of four. Read his post to find out why and how to use the quirks of the Honors program to your […]


While I can appreciate the work done to determine this, it seems that using Omaha, probably not the center of tourist attention, rather than a more traveled destination. Guess I’ll check places like Chicago, San Francisco and NYC to see if this alleged “math” follows.

[…] Hilton’s funny math: save points by extending a stay […]


I love how Hilton points are so easy to obtain but I hate their dynamic pricing.

Buddy M.

Just had a quick question. I have the amex ascend card and am currently close to the 15k in spend to get the free weekend night. Recently when I logged into amex there was an offer to upgrade to the aspire and get 150k points for 4k in spend. Also mentioned that you get a free weekend night and the one every year upon renewal. If I wait until I complete the 15k spend and then upgrade would I then get another weekend night or am I reading the terms wrong? I will probably upgrade anyway as the banner said I was already approved and it wouldn’t change my account number. Just hope the offer lasts until late October as I would want to use the night(s) for a trip in early Oct. 2019. Thanks.


It’s tangential, but Hyatt does this with revenue bookings. It’s completely annoying


I’m a true-blue HHonors loyalist and I’ve been doing these kinds of comparisons for years, Nick. Not only with the original booking, but I go back in every once in a while to see if I can do better. I figure we’re smarter than their computer … or is it that we have more time to chase this stuff?


I have an upcoming reservation at a Homewood Suites in Carlsbad. After reading your post, I thought I should check the points for each night vs the entire stay. I originally booked for 159,000 points but upon checking the entire stay again, the points required was only 156,000. I cancelled and re-booked, saving 3,000 points. I’ve never thought to keep checking rates for upcoming stays.


I booked NYE at double tree by hilton in amsterdam. Cash price was about €650 and charging points only 60k. I immediately took the advantage. Next day, i checked the price again and cash price was the same but points required 250,000.


It’s a great property, paid about 180€ 2 years ago, must have been NYE pricing, nice points redemption


“I’m about the closest thing you’ll find to a Hilton fanboy in the blogosphere”

OMG, *you’re* DCS??


What’s DCS?


We just finished a three night stay in Adelaide that I booked with points. When I booked it several months ago it was 20,000 points cheaper to book as a four night stay. Because we we spending the first night at a B&B in Mclaren Vale we through away the first night. I called the hotel just to make sure they knew and everything was fine. When we checked in a day latter our Diamond status paid off and we were upgraded to a terrific suite!