Why January 2026 is the year I’m finally done with hotel loyalty points
If you are currently paying full price for a hotel room in January, you are basically just subsidizing some CEO’s third vacation home. I’m serious. January is the one month where the entire hospitality industry is nursing a massive hangover from the holidays and staring at empty spreadsheets. They are desperate. And in 2026, because the first of the year falls on a Thursday, that ‘dead zone’ where prices crater is going to be even more aggressive than usual.
The January 2026 ‘Dead Zone’ is actually real
I’ve spent way too much time looking at the 2026 calendar. Most people are going to drag their holiday leave into that first weekend of the year, and then, right around Monday, January 5th, the travel world just… stops. It’s a cliff. I’ve tracked the rates for the Ace Hotel in Chicago for the last three years, and the price drop from December 29th to January 6th is usually around 60%. In 2026, I’m betting it hits 65% because the business travel circuit doesn’t really ramp up until the third week of the month.
What I mean is—actually, let me put it differently. You don’t need a coupon code. You just need to show up when nobody else wants to be there. I used to think booking six months in advance was the move. I was completely wrong. For January travel, the sweet spot is actually about 14 days out. That’s when the revenue managers start panicking about 30% occupancy and start dumping inventory onto the last-minute sites.
It’s simple math. Total desperation.
That one time I tried to be ‘smart’ in Manhattan
I learned this the hard way back in January 2023. I booked this ‘unbeatable’ deal at The Jane in NYC. I thought I was a genius getting a room for $110 in the West Village. What I didn’t realize is that ‘historic charm’ in January just means the radiator clanks like a dying radiator (obviously) and the windows have the insulation thickness of a single sheet of paper. I spent three nights wearing a beanie to bed and shivering under a duvet that smelled faintly of mothballs.
The lesson wasn’t ‘don’t book cheap hotels.’ The lesson was that in January, you can get the 4-star places for what the 2-star places cost in June. Why would you stay in a drafty bunk room when the Arlo or the Public is probably sitting at half-capacity? I was being cheap for the sake of being cheap, and I paid for it with a sinus infection. Never again.
Pro tip: If the hotel website says “historic” and it’s under $150 in a major city, check the heating situation in the reviews. Seriously.
The brands I’m blacklisting (and why you should too)
I know people will disagree with me on this, and honestly, I don’t care, but I am officially done with Moxy hotels. I don’t care how many ‘deals’ they run in January 2026. I’m tired of the ‘check-in at the bar’ gimmick. I’m a grown adult; I don’t want a complimentary watered-down cocktail in a plastic cup while I’m trying to get my room key. I want a desk. I want a closet that isn’t just three pegs on a wall. Moxy is just a dorm room for people who think they’re still in their twenties, and the ‘deals’ they offer are usually just a way to trick you into paying a $30 ‘destination fee’ for a gym you’ll never use.
I’m also losing my mind over Marriott Bonvoy in general. The points have become basically worthless. I checked a few dummy dates for Lisbon in mid-January 2026. A standard room at a mid-tier Marriott property was 40,000 points or $140 cash. If you do the math, that is a terrible redemption. You are better off hoarding your points for a random Tuesday in July and just paying the cash rate in January.
Anyway, I’m getting off track. The point is that brand loyalty is a trap when the market is this soft.
Where the actual money is moving in 2026
If you’re looking for the absolute best bang for your buck in January 2026, look at these three spots. I’ve been digging into the pricing trends and these are the outliers:
- Lisbon, Portugal: It’s not ‘beach weather,’ but it’s 60 degrees and the boutique hotels in Alfama are practically giving rooms away. You can find high-end spots for under $120.
- Chicago: Yes, it’s freezing. But the luxury hotels on the Magnificent Mile (like the Park Hyatt) drop their rates so low it’s almost insulting. If you stay inside and eat good food, it’s the best city trip you’ll ever have.
- Mexico City: This is the one exception to the ‘cold’ rule. It’s perfect weather, but because everyone goes to Tulum or Cancun in January, the city hotels actually have some decent wiggle room if you avoid the first week.
I might be wrong about Mexico City—it’s getting more popular every year—but the data from my own bookings over the last two years shows a distinct dip in the second week of January. I tracked 12 different Airbnbs and hotels in Roma Norte, and the average price dropped by 22% between Jan 4th and Jan 12th.
I’ve bought the same $120 boots four times because I like them, and I’ll keep booking the same boring Hilton Garden Inn in certain cities if the price is right. I don’t need a ‘paradigm shift.’ I just want a clean room that doesn’t cost a week’s salary.
Is it weird that I actually look forward to the travel slump? There’s something peaceful about a hotel lobby that isn’t screaming with tourists or screaming kids on winter break. Just me, a laptop, and a room that I got for 40% off because I was willing to travel when the weather sucks.
Will the ‘points’ people ever realize they’re being played? Probably not. But I’ll be in a 5-star bed in Lisbon for the price of a Motel 6.
That’s the whole trick.
