Earning free Hilton nights is easier than you think! I recommend leveraging new welcome bonuses on Hilton cards ONLY when they are elevated and come with the Free Night Certificates (like our $3,500/night boutique all inclusive stay).

The strategy here is for both you AND your partner to go for one of these offers when they come with the FNC’s – and then combine alllll your earnings together for one insane really high ticket stay (without the $$$ price tag!)

Peep below all the Hilton offers- you cannot go wrong with ANY of these, just depends on what is a best fit for your family and the specific property you are eyeing!

💳 Hilton Honors American Express Card

$0 annual fee (Rates&Fees)

• 7x points on Hotels & Resorts for eligible purchases made directly with hotels and resorts in the Hilton portfolio
• 5x points at U.S. restaurants, U.S. supermarkets and U.S. gas stations
• No foreign transaction fees
• Silver status included (not terribly valuable IMO)

💳 Hilton Honors American Express Surpass® Card

$150 annual fee (Rates&Fees)

• 12x points on Hotels & Resorts for eligible purchases made directly with hotels and resorts in the Hilton portfolio
• 6x points at U.S. restaurants, U.S. supermarkets + U.S. gas stations
• Up to $200 back annually: $50 in statement credits each quarter for purchases made directly with a property in the Hilton portfolio on your Hilton Honors American Express Surpass® Card.
• Earn a SECOND Free Night Certificate after $15k spend in a calendar year
• Hilton Honors™ Gold status included! (Free Breakfast/credit + room upgrades when available!)

💳 Hilton Honors American Express Business Card

$195 annual fee (Rates&Fees)

Remember! Have a side hustle, freelance income, or small biz? (Reselling, content creation, direct sales… it COUNTS). ANY means you make money outside a traditional W-2 qualifies you for business cards.

See my free PDF HERE on how to apply for business cards as a sole proprietor.

This is the most elevated offer of the bunch right now, and it doesn’t touch that 5/24 status or your personal credit long term.

• 12x points on Hotels & Resorts for eligible purchases made directly with hotels and resorts in the Hilton portfolio
• 5X Hilton points on other eligible purchases on the first $100K in eligible purchases per calendar year (3x Points thereafter)
• Up to $240 back annually: $60 in statement credits each quarter for purchases made directly with a property in the Hilton portfolio
• Hilton Honors™ Gold status included! (Free Breakfast/credit + room upgrades when available!)
• Doesn’t count against your Chase 5/24 status or impact your personal credit long term!!

But About The Free Night Certificates… 👀

Hilton Free Night Certificates are genuinely some of the most powerful in ALL of hotel loyalty.

That’s because they are UNCAPPED.

i.e. you can use them on ANY standard night at ANY property. (Even $3,500 boutique all inclusives)

Unlike other hotel program certificates that cap out at a certain category, your Hilton Free Night Certificates can provide huge outsized value that others cannot.

One welcome offer when elevated or one annual renewal = potentially a $1,500-2,000+ night for FREE.

I will never get over this. 😭

➡️ Free Night Certificates expire 12 months after earning them so have a PLAN for these points

➡️ Certificates cannot be combined with points (and don’t need to be when they are uncapped!)

➡️ Certificates cannot be transferred to another Hilton member (just email the hotel and ask them to merge your reservations!)

➡️ Hilton offers $0 resort fees on all points + certificate bookings!

The key: You need standard room award availability at your dream property. Use Hilton’s flexible date calendar to nail down those standard nights.

At VERY aspirational properties this can take some flexibility on dates and booking early… but it exists and is 100% possible!

✨ Dream Properties to Book With Hilton Points + Certificates

OKAY. My favorite part of this whole post. Let’s talk about where these points and certs can actually TAKE you..

🏝️ All-Out Luxury

• Waldorf Astoria Maldives Ithaafushi: Overwater villas, multiple restaurants, private beach… cash rates $2,000+/night. Your cert? FREE. PINCH ME.
• Conrad Bora Bora Nui: THAT turquoise water. Cash rates $2,600+/night. Free Night Cert = zero dollars. 😭
• Waldorf Astoria Los Cabos Pedregal: Cliffside infinity pools, private plunge pools, stunning boat arrival… consistently one of the BEST cert redemptions in the whole points world.
• Bluefields Bay Villas Jamaica: All inclusive with private villas in the Caribbean
• S Hotel Montego Bay: Another high-end Jamaica all inclusive!
• Waldorf Astoria Monarch Beach: Easy domestic long weekend trip on the gorgeous California coast

🌺 Hawaii Without Paying Hawaii Prices

• Grand Wailea, A Waldorf Astoria Resort (Maui): NINE pools, right on the beach, just finished a massive reno. Cash rates $1,000-2,000+/night. An iconic Hawaii family trip on points.
• Hilton Waikoloa Village (Big Island): Saltwater lagoon, dolphin encounters, trams between buildings… THE quintessential big family Hawaii resort. Points stays also waive the resort fee (adds up fast!).
• Hale Hokuala Kauai (Curio Collection): Brand new property opening on the Garden Island soon!

🌍 Europe on Points

• Waldorf Astoria Amsterdam: Inside a stunning canal house on the Herengracht. Dreamy doesn’t cover it.
• Conrad London St. James: Gorgeous central London base. Use your cert here and spend your cash budget on experiences instead.
• Cap Rocat: An SLH boutique hotel in Mallorca
• Hilton Lake Como: The VIEW!!
• Grand Hotel Victoria Concept and Spa: Really high end property in Lake Como

🏡 SLH Properties (This Is Where It Gets REALLYYY Good)

Hilton has partnered with SLH (Small Luxury Hotels of the World) meaning you can now use Hilton points and Free Night Certs at 500+ of the world’s most special boutique properties. Think intimate, one-of-a-kind, how is this even real…

• Hermitage Bay, Antigua (100/10 recommend!!!): Only 30 villas, all-inclusive, two Michelin Keys. We booked this for $0 with Hilton points and it is our BEST redemption to date.
• Tabacón Thermal Resort, Costa Rica: Volcanic hot springs and thermal rivers running through the property at the foot of Arenal Volcano. A family Costa Rica trip on POINTS… come onnn.
• Sowaka, Kyoto, Japan: Intimate ryokan-style property in the heart of Kyoto. Japan bucket list trip? Build it around this stay.
• Cap Rocat, Mallorca, Spain: A converted military fortress on the cliffs of Mallorca. Cash rates $2,000+/night. European family bucket list = UNLOCKED.
• South Bank: A newer boutique property in Turks & Caicos! The standard room is a 2bed “Boathouse”!
• Canaves Oia Suites: Boutique property in Santorini with INSANE views

Also a plug for a beachy family friendly stay at The Hilton Los Cabos (we LOVE this property!!)

💳 Learn how to apply for the Hilton Honors American Express Business Card

💳 Learn how to apply for the Hilton Honors American Express Surpass® Card

💳 Learn how to apply for the Hilton Honors American Express Card