It sounds like the difficulty is mostly in the "book train", "book flight", and "book hotel" steps along with the associated rollback actions. Booking.com and Expedia probably have built their moat around aggregating these steps. If anyone works in this industry, I'd love to know if that's not the case.

This is what booking.com kind of tries to do, but I think it's actually a pretty hard problem not only because of scheduling quirks, but often times stuff being delayed, bad weather, etc. will totally throw a wrench into plans.

It would be nice to book a trip with planned contingencies. So basically, no matter what happens, you'll have something to do. This seems kind of a luxury product though, so I'm not sure how many people would be interested in paying a premium.

I knew a guy who was a public speaker. He would be engaged to do keynotes at conferences, or talks at big offsite corporate retreats, stuff like that. He would always book two, sometimes three flights to events that he absolutely could not miss, so that if one flight was canceled, he would just take a different one without having to hassle with a rebooking under time pressure.

You can't really do it perfectly unless a single site handles all the booking, otherwise you have race conditions, and obviously there's no incentive for airlines, hotels, etc. to give up booking to a third party since they can upsell you on insurance, upgrades, etc.

> and obviously there's no incentive for airlines, hotels, etc. to give up booking to a third party

Airlines, hotels, etc give up booking all the time to third parties. That's what booking.com is.

No, they aren't giving up booking. They are extending booking to a third party. To solve the problem with race conditions (You book the last seat on the airline, I book the last hotel room, and neither one of us can finish the transaction) you have to centralize all the booking in one party, which no one will do because they want to be able to upsell you at checkout.

I can't remember if it was booking.com or some other site like travelocity, but I booked a hotel for work in Dublin, I arrived, and they couldn't find my reservation. After about 30 minutes of the desk staff confusingly clicking around on a computer they 'found' it and I was able to check in. This was a modern hotel too. I stopped using those sites and now only book through the hotel's website, even if it costs more.

For years I was traveling for work, 300+ days a year. I used booking.com almost exclusively and never had this problem.

I did however run into an even worse bug on their platform once where my card got billed, but right after the website crashed and a confirmation never was sent. Naturally, this happened when I had little funds myself.

I called customer support and without a booking number they couldn’t do anything, which I naturally never received…

Thankfully, the money was refunded within 24 hours.

Still I use booking.com, I consider it a great service.

They are not perfect, but they do provide value. My wife does not take showers more than once or twice a year; she takes a bath. Usually twice a day. This is a surprisingly difficult piece of information to find on hotel websites. Booking.com will at least tell you if the property has rooms with bathtubs.

I have resorted to making most reservations by phone, rather than Internet, because it’s the only way to be sure. I don’t like it, it wastes my time, but I have a specific person I can call out who flat-out lied to me if I get there and the room has no bathtub. That is usually enough to get the manager to upgrade me to a room that has the one amenity I specifically requested as a condition of booking.

That’s a lot of water!!

My city takes its water from a surface reservoir and empties its treated sewage into the same river. And I live in the southeastern US, so we have plenty of rainfall.

I’m not draining an aquifer. Other than the cost of the treated water, there is no practical limit to use (the city is nowhere nearly large enough to stress the supply). There are golf courses near the river that just filter out the silt and pump it directly onto the courses.

I rather think what booking.com is really trying to do is to get money from car rental and flight ticket companies for embedding links to their sales.

I mean, it's meant to bring benefit to them, not to the user.

I’ve been thinking of solving (something slightly more complex than) that with simulated annealing. Getting all those variables to line up is hard. NP hard. My use was setting a couple loose params for vacation (beach, flight <8 hours, flexible dates) and having it find me the full package.

Funny thing is this is already a job when I thought about it. Travel agents used to do this, now it feels like going to a “financial advisor” where they are more interested in selling you the package with a kickback

A solution to this is to book your flight first, then the hotel, as all airlines (that I'm aware of) allow for a full refund within 24 hrs.

a variation of this problem is carrying your shopping cart around. A shopping list that you can buy in place A or B. Also splitting shopping wisely in both.

Packagers do this. V2 is to throw your negotiations agent into the mix… we are going to book all 3 of these, now, but you need to give us a kickback.

Not booking, but there are tools can search all the options and give you the links to book by yourself.