I’m briefly in New York, and decided to check out the iconic Waldorf Astoria New York, which recently reopened after a massive renovation. While I’ll share some initial thoughts shortly, in this post I’d like to talk about an interesting occurrence at check-in, as I’m curious how others feel about this…

Waldorf Astoria offers junior suite upgrade for $200

I redeemed a Hilton Honors free night award to stay at the Waldorf Astoria New York for one night. The hotel has 375 rooms and suites, and a vast majority of the accommodations at the hotel are suites (initially the plan was for the hotel to be all-suite, but they backtracked, and added a small number of non-suites, I guess).

For what it’s worth, standard room points bookings confirm into the “king room” category. Ahead of check-in, I noticed that I had been upgraded one category as a Hilton Honors Diamond member, to a “deluxe king room,” This retails for $92 more, so it’s better than nothing, but also certainly not a very exciting upgrade (which basically sums up my expectation of Diamond upgrades in the United States).

I was totally fine with that, and was happy to just be staying there with a free night award. At check-in, the front desk associated informed me that I had been upgraded to a deluxe king room. I didn’t ask about a further upgrade, but before being given keys, he shared what was supposed to sound like an enticing offer — he asked if I wanted to upgrade to a junior suite for just $200 more, and then he explained the features of the room.

For context, below is how much the three entry level king room categories were retailing for on the night I’m staying.

This was the first time I’ve been offered an upgrade like this

Hotels selling upgrades for cash is nothing new. However, as a fairly high tier elite member, I’ve never been offered what would be a pretty standard elite upgrade for cash at check-in. After all, an upgrade from what I booked to a junior suite would be “only” two categories, which hardly feels like an overly generous upgrade.

Now, I’d like to think that I have reasonable expectations with Hilton Honors Diamond upgrades. If you look at how Hilton’s upgrade benefit is published, it says the following, which sounds quite generous:

Space-available room upgrades
If we have a better room available, it’s yours – up to a 1-bedroom suite.

However, when you look at the terms, you’ll see the following:

Diamond Hilton Honors Members may receive upgrades to preferred rooms, based on availability at the time of arrival. Upgrades for Diamond Hilton Honors Members may include upgrades up to “junior”, “standard” or “one-bedroom” suites.

As I interpret it, hotels have have discretion as to what types of rooms they upgrade you to. So while some people will disagree with me, I don’t think the hotel was technically doing anything wrong by providing me with some sort of an upgrade, and then trying to sell me an additional upgrade. However, it definitely doesn’t make a great first impression. It’s one thing if the cash upgrade were to a speciality suite, but we’re talking about the most entry level suite here…

What most rubbed me the wrong way was the upgrade price. It was made to sound like it was some sort of a bargain, and in theory, getting a suite upgrade for $200 might not sound bad. However:

• The deluxe king rooms are 575 square feet, while the junior suites are 620 square feet, so we’re talking about a room that’s 7% bigger
• The $200 upgrade amount was actually greater than the price difference in the first place between the most basic room and a junior suite ($184)
• If you’re going to offer someone a paid upgrade, I think it should be (at most) the price difference between the room you’re blocked in and being promised vs. the room you’d be upgraded to; if they’re telling me I’m getting a deluxe king room ($1,077) and they offer me a junior suite ($1,169) for cash, I shouldn’t be on the hook for more than $92, in my opinion

Anyway, I rejected the upgrade, and was ultimately very happy with the room I got. Still, I found it to be an interesting interaction, as it’s the first time that I’ve been offered such a modest paid upgrade as an elite member, all while being asked to pay more than the rate difference between rooms.

Bottom line

While hotels frequently sell upgrades, I was a bit surprised to be offered a cash upgrade to two categories above what I booked while checking in at the Waldorf Astoria New York as a Hilton Honors Diamond member.

What surprised me most was the extent to which this wasn’t a deal — the upgrade price was more than the difference in rates between an entry level room and a junior suite, and way more than the price difference between what I was blocked in and what I was being offered.

What do you make of this upgrade “offer,” and how would you have handled it?