Best Deals on Hilton Stays

5th Night Free Hilton Award Stays for Hilton Silver
& Higher Status

Did you know that anyone with Silver (or higher) Hilton status gets the 5th night free on Hilton award stays? This is for a stay of 5 consecutive nights.
You’ll stay 5 but only need points for 4 nights. Pretty sweet.

We personally have Hilton Gold status from holding The Platinum Card® from American Express. If you have this card, you simply have to go into the benefits section & enroll in this benefit by linking your Hilton Honors number. *Terms apply to American Express benefits and offers. Enrollment may be required for select American Express benefits and offers. Visit americanexpress.com to learn more.

Other cards that give you Hilton Status:
Hilton Honors American Express Surpass® Card – gives you gold status
The Hilton Honors American Express Business Card – gives you gold status
Hilton Honors American Express Aspire Card – gives you diamond status
The Business Platinum Card® from American Express – gives you gold status*
*Terms apply to American Express benefits and offers. Enrollment may be required for select American Express benefits and offers. Visit americanexpress.com to learn more.

Getting Amazing Value from 5th Night Free

I’m using the Grand Wailea, A Waldorf Astoria Resort, in Maui for this example (But you can use this technique for any Hilton!). This is a bucket list property for many people, with rates often over $1K PER NIGHT!

The first thing you want to do, is find 5 nights in a row with the lowest nightly point options (to get the lowest rate, all 5 nights must have this rate). Select “flexible travel dates” and choose ONE night to see a calendar like this giving you the nightly rate.

So here you can see, we could visit July 1 – 6.
Each night is 110K points. If you are able get the 5th night free on award stays (by having silver status or higher), you’ll only need 440K points for this 5 night stay.

What If You Don’t Have Hilton Points?

But let’s say you don’t have any Hilton points (or you don’t have enough)…
There is another option and it’s one we don’t talk about often because we love getting super discounted travel WITH points…

It’s buying the points you need when there is a special 100% bonus purchase offer (Hilton has these several times a year, so if they don’t have one right now, keep checking):

it’s important to know, this pricing varies a lot – be sure to check current options

This could be a great option if you don’t have any/enough points.
Paying $2200 for the points instead of $6600+ for the 5 night stay is a GREAT deal.
The 5th night free on award stays just makes using points (even purchased ones) a great deal!

Have You Purchased Points Before?

Purchasing points is often not my first option, because I want to spend very little out of pocket and use points. BUT when you don’t have the points, buying them can be an amazing option.

With the current costs shown above, you are paying ONLY $440 per night for your 5 night stay!
And as you can see, the nightly rate is $1132+.
So in this instance, buying points could be a pretty incredible deal for this property.

Thank you for supporting my small business! When you use my affiliate links to apply for a credit card, I earn a commission from the bank. But you still get the same great offer! And this helps me keep my guides and personal help free.

Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.