Hotel Hopping in 2025: Who Won My Loyalty for 2026?

Hey friends, what's up? Phillip here with Points With Phillip, and today I'm going to give you a full rundown of my past year with hotel stays. More importantly, we're going to figure out which program is likely to be my preferred one moving forward into 2026.

For those of you who don't know, I'm rocking two high-profile, high-annual-fee travel cards tied to hotel chains: the Hilton Aspire card (with its $550 annual fee) and the Ritz-Carlton card. Going into last year, my perception was that Hilton, with my Diamond status, would be my primary program, and Marriott, with my Gold Elite status, would be secondary.

I've stayed at three major hotel chains this past year: Marriott, Hilton, and Hyatt. We'll talk about my favorite stays, where I stayed, and ultimately, what I think might be my personal favorite going into the new year. Let's get into it!

Hilton: High Expectations, High Highs, and a Few Lows

With Hilton Diamond status via my Aspire card, I definitely had high expectations. And many times, Hilton delivered!

• Conrad London St. James (December 2024 & March 2025): My wife and I stayed here twice during our European trips.

  • December Stay: Even though we paid cash (via Hotel Collection), Diamond status was a game-changer. Arriving at 8 AM after an overnight flight, we were granted immediate access to the Executive Lounge. We refreshed in the shower suites, enjoyed breakfast by a roaring fireplace, dropped our bags, and started exploring London feeling completely refreshed. The service was impeccable, with free breakfast, lounge access (snacks, drinks, and tranquility!), and an amazing turndown service complete with chamomile pillow spray and mints.

  • March Stay: I accidentally booked a non-refundable stay for February instead of March, which was substantially cheaper. By all accounts, I was "up a creek," but a call to the Diamond line and a direct message to the property through the Hilton app saved the day. They rebooked my stay at the February rate, saving us around $300 a night! They absolutely didn't have to do that. We also received a fantastic upgrade to a rooftop room with a view of Westminster Abbey. This property truly showcased the power of Diamond status and outstanding service.

• Canopy by Hilton Paris Eiffel Tower (March 2025): We used Hilton points and a free night award here. This is the closest Hilton to the Eiffel Tower, and it was phenomenal. The day before arrival, we were upgraded to a King Junior Suite with a balcony. I even got to choose our room, securing one with a direct Eiffel Tower view from our balcony! Free hot breakfast (including an omelet and waffle bar) was included, and the staff were incredible.

• Canopy by Hilton West Palm Beach (June 2025): A two-night stay paid for through the Amex Hotel Collection credit. This included a $100 property credit (for food) plus an additional $15 per person per night in food credit. We loved the rooftop bar and pool, maximizing our credits for meals and drinks.

• Conrad Fort Lauderdale Beach (June 2025): Booked through Fine Hotels & Resorts (FHR), we received an upgrade to a one-bedroom ocean view suite. We were told about our FHR $100 credit and $25 per person per night Diamond food credit. However, at checkout, the front desk denied the Diamond credits, stating it was "either/or" with FHR. After numerous calls and messages, the general manager reluctantly gave me a "one-time benefit" for being a Diamond member, implying I had misheard. Haggling over $50 at a luxury property left a sour taste.

• Hampton Inn Louisville (date not specified): A basic, older but renovated airport hotel. Diamond benefit: two free canned Cokes per night. Low expectations met.

• Caribe Hilton San Juan (date not specified): We had multiple stays here, using points for some nights (which waived the $50/night resort fee) and cash for one night to use my Hilton Aspire credit. We got a cool room in the beach wing. The free continental breakfast was standard, but the $20/person upgrade for a hot breakfast wasn't worth it. While a great resort, I felt the Diamond benefits fell a bit short compared to international properties.

Hilton Takeaway: Internationally, Hilton's Diamond status recognition was far superior. Domestically, particularly at the Conrad Fort Lauderdale and the Caribe Hilton, I experienced frustration due to perceived lapses in benefit delivery. While I had the highest expectations for Hilton, these high expectations also led to the most disappointment. I also have to consider Hilton's point changes – rooms can now reach 250,000 points, and while the 1:2 transfer ratio with American Express is good, 50,000 Membership Rewards points for a 100,000-point Hilton room can also get me a business class ticket overseas, or multiple premium economy seats.

Marriott: Solid Stays with Gold Status

With only Gold Elite status, my expectations for Marriott were lower, and they delivered consistently good experiences.

• La Metropolitan Paris Tour Eiffel, Tribute Portfolio (December 2024): A fantastic use of a free night certificate from my Bonvoy Boundless card. Just half a block from my excellent Canopy Hilton stay, this property had a beautiful lobby, wonderful staff (offering umbrellas during rain!), and a cool Asian restaurant. We had a charming second-floor room with a Juliet balcony, perfect for the December weather.

• AC Hotel Downtown Huntsville (July 2025): A point-based stay where my 35,000-point free night award covered a night that would have cost $300-$350 cash. Modern, cool, and in a great downtown location.

• AC Hotel Atlanta Perimeter (date not specified): Another points stay (18,000 points/night). A nice, cheap hotel close to where we wanted to be. The only minor hiccup was an AC issue that required us to re-room, but it was handled promptly.

Marriott Takeaway: My Marriott stays offered good value for points, and I was generally happy with the experience given my Gold status. While I didn't get free breakfast, the properties were clean, modern, and in good locations.

Hyatt: Aspirational vs. Basic

Hyatt holds a special place, especially as a strong transfer partner, even without status.

• Park Hyatt New York (December 2024): For our anniversary, I bought points when they were on sale and snagged a room that would have cost $1,500 cash. We received an upgrade to a junior suite with a Central Park view – a huge room with a sitting area. Room service was an event, with the entire table set up in our room. An incredible, aspirational stay. No free breakfast, but that was expected without status.

• Hyatt Regency Capitol Hill (July 2025): Transferred 50,000 points for a two-night stay during July 4th week. An older property undergoing renovations, our room was newly renovated (it still smelled like fresh drywall!). Good location, just a block from Capitol Hill, though the view was unremarkable.

• Hyatt Place Greenville (November 2025): At 5,000 points a night (or about $90 cash), this was a basic experience. The elevator was finicky, the room door barely latched, and the WiFi was terrible (I couldn't even upload a video!). While you don't expect much from a Hyatt Place, this was definitely a low point.

Hyatt Takeaway: Hyatt remains an incredibly strong transfer partner, offering amazing value for aspirational stays at their higher-end properties. However, without status, lower-tier properties are just basic hotels, underscoring that points strategy is key here.

My Preferred Program for 2026?

So, after all that, where do I stand for 2026?

I had the most frustrations with Hilton, but primarily because I also had the highest expectations due to my Diamond status and the caliber of properties we often chose. When Hilton delivered, it was truly exceptional. However, the point devaluations and inconsistent benefit recognition at some domestic properties are concerns.

Hyatt's point system and transfer partner strength remain incredibly appealing for those aspirational stays, but I still lack meaningful status there. Marriott provided solid, no-frills stays that met expectations for my Gold status.

Moving forward, while many of our planned November stays are still with Hilton, I think my strong brand loyalty to Hilton will lessen. I'll definitely be more willing to factor in the specific location, the property type, and which points I have readily available when making a booking. I won't default to Hilton as much as I have in the past.

The goal is to maximize value, whether it's through status, points, or cash, and sometimes that means spreading the love across different hotel programs.

Let me know in the comments section below what you guys think – which hotel program is winning your loyalty, and why?