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One of the major benefits of the Hilton Honors loyalty program is the “fifth night free” benefit when redeeming your points. The name is a little misleading, however, because you don’t actually pay for the first four nights and then get the fifth night for free. But you do get a discount that makes it highly worthwhile to book your Hilton award stays in blocks of five nights.

Who Qualifies for the Fifth Night Free Benefit?

Only Honors members with Silver, Gold or Diamond status are able to take advantage of the fifth night free benefit.

Luckily, Silver status is ridiculously easy to achieve. In 2021, you will only need 2 stays or 5 nights.

How Does Hilton Calculate the “Fifth Night Free” Benefit?

Because award pricing can fluctuate from night to night, Hilton calculates the average points cost per night across all nights of any award stay of 5 nights or longer. Hilton then deducts the cost of one night. You can see an example on the Hilton Honors website (reproduced below).

Why Does it Work This Way?

If you consider yourself a “travel hacker” or simply want to extract maximum value from your points, you will book a stay that is exactly five nights long (or ten or fifteen…). If you do, you will receive a 20% discount (in points).

Five nights, however, is too many for a “long weekend” getaway and too short for a week-long holiday. So many people simply go ahead and book a seven-night award stay. However you wouldn’t be entitled to a 20% discount. Extending Hilton’s example from above…

• 3 Nights Peak – 3 x 40,000 = 120,000 points
• 4 Nights Off-peak – 4 x 30,000 = 120,000 points

Equals a total of 240,000 points, or 34,300 points per night. In this scenario, you would only receive one free night and would pay 240,000 – 34,300 = 205,700 points.

Do I Get the Fifth Night Free Benefit When Paying Cash (or Points & Money)?

Short answer = NO.  This benefit only applies to award stays using ONLY points.

If you don’t have enough points to pay for four nights using ONLY points, you will be unable to enjoy this benefit.

Do I Get the Fifth Night Free Benefit When Booking a Premium Room?

Again… NO.  You only benefit from the fifth night free when booking standard rooms using points.

But I Only Want to Stay Four Nights?

Well.. you are out of luck. But many people still book a five-night award stay and depart a day early without informing the front desk or checking out. Even though that final night is essentially a “mattress run”, the extra night credited to your Honors account might come in handy for elite status purposes one day…

Bottom Line

Even though it can be a bit awkward to organise your holidays to spend exactly five nights at the same hotel, booking a five-night award stay is the best way to extract maximum value from your Hilton points.