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Old Nov 23, 2023, 9:47 am
  #1  
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Hilton Elite 5th night free when using points

Am I able to schedule 2 consecutive 4 night stays to take advantage of "5th night free" at the same Hilton property? We are planning a 10 night stay paying with points and just curious if this is allowed.
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Old Nov 23, 2023, 9:53 am
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No need to book two stays. Just book one stay for 10 nights and you should be charged for 8.
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Old Nov 23, 2023, 9:55 am
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Originally Posted by taore
Am I able to schedule 2 consecutive 4 night stays to take advantage of "5th night free" at the same Hilton property? We are planning a 10 night stay paying with points and just curious if this is allowed.
Just make one reservation for all 10 nights.

When you go to checkout, the two "fifth night free's" will be automatically calculated and the total points required reduced by 2x nights.
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Old Nov 24, 2023, 2:44 am
  #4  
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It's still worth checking two consecutive 5-night stays. Sometimes the "fifth night free" algorithm results in a slightly cheaper stay overall that way.
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Old Nov 24, 2023, 11:19 am
  #5  
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To pick a nit, the Fifth Night Free is not a Diamond benefit, unless something has changed post-Covid. I know I received it as Gold and I believe Silver gets it.
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Old Nov 25, 2023, 8:29 am
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Per About Hilton Honors - FAQ and Details on the Program

What do I have to do to receive the 5th Night Free Elite Benefit on Reward Stays? 5th Night Free is a benefit for our Silver, Gold and Diamond Elite Hilton Honors Members. Please make sure you are logged into your Hilton Honors account to automatically receive the benefit on qualifying stays.

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Old Nov 27, 2023, 2:06 pm
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I believe up to 4x of the 5th night free can be used in one reservation. If you need to book 25 nights and want to break it up, you might need 2 reservations, but for 10 nights you are fine
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Old Nov 28, 2023, 4:25 am
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More questions

I do have 3 separate stays - 2 five night ones and then 2 more nights. Am I misremembering or is it best to have some charge on each reservation (like a glass wine) to get points for the stay ?
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Old Nov 28, 2023, 4:00 pm
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Originally Posted by serpens (Post # 5)
To pick a nit, the Fifth Night Free is not a Diamond benefit, unless something has changed post-Covid. I know I received it as Gold and I believe Silver gets it.
Excellent catch!

The thread title has been helpfully changed from "Diamond" to "Hilton Elite" to reflect your insight and the terms of the FAQ in the post immediately after yours.
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Old Nov 29, 2023, 8:11 am
  #10  
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Originally Posted by SPN Lifer
[...] to reflect your insight and the terms of the FAQ in the post immediately after yours.
Well, I was working from memory, without confirming that nothing had changed. Credit should be given to rabilancia, who confirmed that it applied to all status levels (I don't believe there is anything below Silver), that it is still current policy, and included a link to the appropriate web page. Well done, rabilancia, and thank you for doing the leg work that I did not do.
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Old Dec 4, 2023, 4:14 am
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No one responded so I will

Originally Posted by FlyfromDenver
I do have 3 separate stays - 2 five night ones and then 2 more nights. Am I misremembering or is it best to have some charge on each reservation (like a glass wine) to get points for the stay ?
The charge wasn’t necessary but having 3 separate stays during the same timeframe did benefit with points for the stay plus bonus points which slightly reduced the number of points for each stay.
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Old Dec 4, 2023, 8:12 am
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Originally Posted by FlyfromDenver
The charge wasn’t necessary but having 3 separate stays during the same timeframe did benefit with points for the stay plus bonus points which slightly reduced the number of points for each stay.
Not sure I follow what you mean
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Old Dec 4, 2023, 12:49 pm
  #13  
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In the past, when paid nights were adjacent to award nights they would get auto-combined into one stay and no points would be earned at all, although I don't think spending on incidentals changed that.

However I do recall a past promo under those old rules, where they gave 2000(?) points per night, but it would only activate on redemptions if you spent something. I remember several hotels where I looked for the cheapest minibar item
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Old Dec 4, 2023, 1:44 pm
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Originally Posted by craigthemif
It's still worth checking two consecutive 5-night stays. Sometimes the "fifth night free" algorithm results in a slightly cheaper stay overall that way.
That used to be true when the value of the free night was, as you say, the product of a calculation. But the benefit has been simply the award cost of the relevant night(s), standing alone, for some time now, so I don’t believe there’s any difference between booking 10 nights vs. two reservations of five nights each.

If that’s wrong, i’d be happy to know why.
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Old Dec 4, 2023, 1:57 pm
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Originally Posted by beltway
That used to be true when the value of the free night was, as you say, the product of a calculation. But the benefit has been simply the award cost of the relevant night(s), standing alone, for some time now, so I don’t believe there’s any difference between booking 10 nights vs. two reservations of five nights each.

If that’s wrong, i’d be happy to know why.
I don't have enough points to check whether:
  1. Night 5 and Night 10 are free
  2. Night 9 and Night 10 are free
If #1, then indeed there ought to be no difference in how you book it...
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