Even if you travel frequently, there are many reasons why you should get a hotel credit card with your favorite brand. Although there are no-annual-fee hotel credit cards, you’ll usually get more value from hotel credit cards that come with annual free nights. After all, an annual free night can potentially provide significantly more value each year than the card’s annual fee.

However, if you plan to use your free night award to stay at a hotel you typically won’t splurge on, multiple free award certificates are useful if you plan to stay more than one night. So, whether you plan to get multiple hotel credit cards with free nights or choose to sign up for the same card and get a travel companion to join you on your trip, you’ll want to plan your credit card applications carefully.

Related: 12 Best Marriott Beach Hotels in the United States

Maximize hotel free night certificates with credit cards

Beach Villas at Le Meridien Maldives Resort and Spa. Katie Genter/The Points Guy

When you apply for a card with an annual free night, it usually comes right after your account anniversary. So, if you time your applications carefully, you can get multiple free nights at the same time each year with the same expiration window (usually 12 months from the issue date). The longer this overlap, the more time you have to combine them at the same property instead of being forced to use them for more than one overnight stay.

My husband and I used three Hilton Free Night Certificates at Conrad Maldives Rangali Island in 2021 and two at Hilton Maldives Amingiri Resort & Spa in 2023. It doesn’t make sense to use just one free night at a Maldives resort and even a standard award night is expensive at these properties if you redeem Hilton Honors points. Hilton Free Night Certificates are especially valuable because you can use them at almost any Hilton property, regardless of the cost of the award night, as long as there is standard award availability.

You can earn Hilton Free Night Certificates with the following cards:

  • Hilton American Express honors the Aspire Card: You will get one free night when opening the card and one every year after your account renewal. Cardholders can also earn a second free night by spending $30,000 on the card in a calendar year and a third night by spending $60,000 in a calendar year.
  • Hilton honors the American Express Surpass® Card: Cardholders can earn a free night certificate after spending $15,000 on eligible purchases on the card in a calendar year.

Information for the Hilton Aspire Card is independently collected by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

Related: Best Hilton hotels and resorts on the beach, from the US to the Maldives

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Beach Villa at Hilton Maldives Amingiri Resort & Spa. Katie Genter/The Points Guy

Multiple Marriott Bonvoy credit cards also offer the ability to earn free night rewards. So, even if you choose to travel solo, you can time your application so that you can earn multiple free night awards at the same time each year.

For example, suppose you have a Marriott Bonvoy Boundless® Credit Card and Marriott Bonvoy Business® American Express® Card. In that case, you’ll receive one free night award valid for one night’s hotel stay at properties with a redemption level of up to 35,000 points after each card’s account anniversary (some hotels have a resort fee). We’ve used multiple Marriott Free Night Awards for multinight stays at several hotels we didn’t book with cash, including Le Meridien Maldives Resort & Spa.

Note that Bonvoy Business Amex cardholders can also earn a second free night award (up to 35,000 points per night) after spending $60,000 in a calendar year (resort fees may apply).

Finally, there’s the World of Hyatt credit card, which offers free nights at category 1-4 properties upon renewal. You can also earn another when you spend $15,000 in a calendar year. If you time your purchases on the card to reach the $15,000 mark around your cardmember anniversary, your free nights can be combined for a two-night stay.

RELATED: Why I Aim to Spend $15K on My World of Hyatt Credit Card Every Year

Many hotel credit cards with annual fees under $100 offer an annual free night, so consider the hotel credit cards you already have before applying for a new card. You can also find your favorite travel companion and apply for a new card at the same time. So, you can enjoy multiple free night awards with the same expiration dates as you plan trips for years to come.

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