My strategy for maximizing Hilton Honors points and free award nights

If you read my blog often enough, you’ll know that I’m a recent convert to the Hilton-portfolio brand of hotels. After signing up for a Hilton American Express business credit card which gave me complimentary gold status, and after a few bed Airbnb experiences, I decided to give Hilton a try.

As a remote worker, I was generally opposed to hotels. My main concern was lack of a kitchen — when I’m traveling, I like to cook my own breakfast because it can often take an hour or two to find a place and get served in a new city (plus, I’m pretty cheap when it comes to food, as I would rather spend that money on travel). However, Hilton since gold status comes with free breakfast, this made me less anxious about switching over.

By staying at Hilton properties more and also with credit card bonuses, I’ve managed to rack up a lot of points and a free weekend night (about to hit my second one!).

While there is some controversy around their actual value, Hilton points are valued at ~0.6 cents per point. That said, with my strategy below, I’ve been able to redeem them for as much as 2 cents per point using some of the strategies below.

For the free weekend night, it’s given as a yearly bonus to certain credit card holders (with the Aspire card), and for those with the business card, you can get this after spending $15,000 in a calendar year (if you spend $40,000, you get 2). This can be used on a standard room and can net you a value of over $750, if used correctly.

How to maximize the value of your Hilton points

1) Get a credit card with complimentary Hilton status

If possible, you should sign up for a Hilton credit card that comes with complimentary status — this includes the Hilton American Express business card or the Hilton Aspire card. The main reason for doing this is that elite members receive their 5th award night free (meaning you’ll only need to pay 4 award nights for a 5 night stay).

Which leads me to my second strategy…

2) Wait until you have enough points to book 4 nights (so you can get your 5th night free)

Rather than redeeming points for a night or two at a hotel, if you do obtain Hilton status, you’re better off waiting until you have enough points (and time) to book 4 nights somewhere so that you can get the 5th one for free. The great thing about Hilton Honors is that it’s very easy to earn a lot of points very quickly, and the credit card bonus sign-ups are very nice right now (some are in the 125,000-150,000). A night at a top property is 95,000 miles (more on that below).

Hilton also regularly has sales on points where they give you a 100% point bonus on anything purchased, which can help you get your balance to where it needs to be. This trick can save you as much as 120,000 points for a standard room.

3) Use points at luxury properties

The best way to maximize your points (aside from staying for 5 nights), is to use them for standard rooms at usually pricey properties. This includes the following hotels:

  • Conrad Maldives
  • The Grand Wailea, a Waldorf Astoria Resort
  • Conrad Tokyo
  • Waldorf Astoria Maldives
  • Conrad Koh Samui
  • Conrad Bora Bora

A standard room at most of these hotels will be 95,000 points, which means you’ll need 360,000 points to get the best redemption.

How to maximize the value of your Hilton free weekend night

If you have the Hilton Aspire card, or if you have the Hilton Business or another card that entitles you to a free weekend night after a certain spend threshold, you should strategy 3 above to maximize your points (i.e., trying to stay at luxury properties).

Keep in mind that the free weekend night only applies to standard rooms, and some hotels don’t have any so-called “standard” rooms (here’s a list of excluded properties– but, luckily, all of the above are not excluded).

So far, my redemptions have been for the Grand Wailea and the Conrad Maldives. I wrote about the Grand Wailea here and am definitely excited to check out the Conrad Maldives later this year!

What’s your favorite way to use Hilton points and free award nights? Let me know in the comments.

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