Assuming everyone here is very aware of Hipmunk (YC S10), but right around the same time that Hipmunk launched with flights there was a hotel startup called Room 77, founded by some travel bigwigs including Brad Gerstner, that unveiled at Launch Festival (https://www.youtube.com/watch?v=DH2b7IUx_14). Room 77 was trying to tackle this exact problem (http://www.tnooz.com/article/room77-has-a-view-to-shake-up-o...).

However, Room 77 just recently announced a licensing deal with Google that indicates somewhat of a pivot to mobile with a portion of their team joining Google (http://skift.com/2014/04/07/room-77-taps-google-for-an-exit-...).

As a lifelong student of hospitality, former hotelier, and now cofounder in a hotel startup, it's highly unlikely that we'll ever see hotels letting travelers pick their own rooms. This would be a logistical nightmare with preparing rooms, early checkins, late checkouts, stayovers, etc. In Vegas forget about it; there are days when a hotel will turn over 1000+ rooms and it would be impossible to do so in an orderly manner. First to checkout are the first cleaned and the first available to whomever is at the front desk. Plain and simple.

Inventory in other hotels can get tricky with numerous bed types, room types, room view upgrades, etc. It sounds like a great idea for travelers, but a nightmare for hotels who would have to deal with irate guests if they didn't get their desired room.

Commodification is a thing right now with hotels (think of all those upsells on planes like extra leg room; a company called Nor1 - http://www.nor1.com/ - is working on streamlining hotel related upgrades) and the 24 hour stay (not so much technology behind this one, it's built into their property management systems). So if you check in at 6pm the first day you have to be out by 6pm the next day (or whatever time you checked in). If the 24 hour thing works, pre-checkin room selection might stand a chance and get built in to as a part of the upgrade process (I'd imagine it'd encourage you pick a better view or room type and for a fee).

You nailed the reason: inventory management. It is much easier to manage rooms as equivalent fungible commodities than as special unique offerings.

Granted, there are a lot of related industries that do offer guests this privilege: theater/opera tickets, tables at fancy restaurants, luxury car rentals, etc. But these are usually luxury offerings, where they can afford to charge more (and charge premiums based on your selection) to offset the greater cost of management.

What happens to the person staying in that room who decides at the last minute to stay an extra day?

I presume they would have to move rooms, same as if that type of room were fully booked out and they decided to extend their stay - they'd be required to move to a different type of room.

Great question. Some BnB hotels and condo rentals do have reservation systems that let you choose the specific room. They tend to be places where each room is unique or separately owned, though.

As for why you can't pick your room in a typical hotel, I'm not in the business but I can imagine the reasons are mostly advantageous only to the hotel. Not really for malicious reasons, but just designed to maximize occupancy. I kinda imagine a Tetris type of board where, if the hotel management is allowed to control it, will be packed with no void spaces - always as close to full capacity as possible. In fact, it will be overbooked with the expectation of cancellations. If they let the visitors control it (i.e. choose your own room) then the schedule will have a lot of void spaces (unbooked days) with the best rooms taken and the less desirable ones unbooked.

There are times when I would pay a premium with no-refund allowed if I could lock in a specific room, though. I'm sure others would as well. There's probably an opportunity for a hotel to do this.

Because, at least in the US, hotels have liberal cancelation policies. In addition, the hotel never really knows what kind of work will be required after a guest leaves...or exactly what time a guest will leave, so the order in which rooms are turned around is not known beforehand. And letting people into their rooms at check-in time or even before is a bigger deal for travellers.

In addition, there are frequent customers who may need a last minute room and companies (such as an airline when a flight is cancelled or overbooked or delayed) that may need a block of rooms on short notice.

An airplane on the other hand is a public space, and the individual has much more limited control over much less space...trash an airline seat and you're probably going to jail.

Aren't most of these things something that a hotel could charge customers? You want to check in at 1 PM instead of the standard 3 PM, OK, that is more money? You want to be able to cancel up to 12 hours before check in, OK, that is more money? We can't guarantee you can't get bumped out of your room just like airlines can't guarantee that you won't get bumped off your flight. It seems like almost all of the same issues with airlines apply to hotels and yet airlines, as bad as they seem to be at customer service, are actually ahead of hotels in this regard and I assume they did it because they could make more money by constantly attempting to up sell customers and it seems hotels could do this as well.

I meant you might get bumped out of your room and even the hotel if you decide to stay another day for which you don't already have a reservation. If you have a prior reservation you can't get bumped. Well, maybe you can. I've never heard of that happening with a hotel but I assume they do overbook and somehow they deal with it.

It's called 'walking the guest' and it happens somewhat frequently. Hotels always overbook when they can and normally it doesn't cause any issues because there are almost always enough cancellations and no-shows to compensate. But it does happen and probably more often than you'd imagine. Typically the late night arrivals will be the ones getting walked, especially if they're only staying for a single night, and even more so if they booked through a third party site like Priceline. I am not sure if it's legally required or not but the hotel that is walking you will usually set you up in a nearby hotel and pay for the first night. Of course if the nearest hotel with an opening is 20 miles away, this could be quite frustrating.

Edit: If you are going to be arriving late, call the hotel in advance and let them know and you greatly decrease the likelihood of getting walked as they will tend to walk someone before you instead.

It would actually seem like a win for everyone as hotels could charge more for rooms that are better just like airlines do for premium seating. That room away from the elevator that is another $25/night. They already do things like that, the ocean view costs more for example.

That seems like a good idea, and I could see hotel visitors wanting to select a room overlooking the parking lot (to watch a vehicle), or wanting to be on a particular side of the building (avoiding highway noise), etc. People have all sorts of little preferences, so I think that feature would get a lot of use. They also like being familiar with a room, so I could see them booking the identical one on their next trip.

Since we're talking about hotels, I think the business in general has a lot of faults. I get more perks at a $10 per night hostel or $50/night Airbnb apartment, than I do at a $300 per night hotel.

When you book a hotel for $300 per night, they nickel and dime you for everything. Wifi? You'll need to register for it at the front desk, and pay $20 per day. Oh, want a bottle of water, or small snack, that's another $10. That hostel, or cheap-o hotel will give you free wifi. I'd say half of the Airbnb places I've stayed at left beer or a bottle of wine in the fridge, and a few places had a giant fresh platter of fruit on the kitchen table.

Why doesn't this happen with a $300 per night hotel? To me, this is a complete turn off. I'll avoid the fancy hotels, because I don't know where it'll end. They're trying to gouge me at every single corner when I've paid a premium, and instead of being an appreciated customer, I feel like I'm being taken advantage of. My parents are well off, and I know they feel the same way. When they go on vacation and stay at a high end hotel, they have to tip people left and right. They're forced to use the staff at the entrance for carrying their bags up to the room, and then they need their wallet ready to tip them for that 2 minutes of work. What kind of awful first impression is that? You're on vacation, paid a small fortune for a room, and within minutes you need to shell out more cash.

Yes, I know their thought process is they can squeeze absurd prices out of people that have money, but I think it's completely backwards and destroys their image and sense of luxury.

I think there's a business for a mid-range hotel with perks. Take a mid-range hotel with $150 per night rooms. Add $15 of free perks, and charge $165 per night for your rooms. With that $15, you could give every visitor free wifi, 2 bottles of water, a couple of bananas/oranges, bag of chips, couple of health bars, bottle of juice, 2 beers or a bottle of wine, and small bag of nuts. To me, that's a huge difference in service and experience for a small price. It would make me book that place every night of the week, and I'd recommend it to others. I'd put employees or clients up in such a place, knowing they're feeling pampered. Why doesn't this exist? Would this not be appealing to anyone else?

I read almost this exact question on reddit a few months ago, and here is the answer someone else gave:

Hotels don't cater to vacationers or casual travelers. They cater to business travelers. Business travelers who aren't using their own money, can expense everything back to their company, and don't really only care about convenience. Hotels know this, and prey on it.

Airbnb/hostels don't cater to business travelers, they cater to casuals, and casuals want everything included.

I did a quick google and found http://www.ahla.com/content.aspx?id=35603 which says that 40% of guests are on business and 60% are leisure travelers. This data is for the the USA for 2012.

Seems believable. I just caught an interview on television earlier today with the CEO of a luxury worldwide hotel, and he said leisure clients went up from about 35% to 45% in the past decade, so it's a growing focus for them.

I've tried searching reddit and google for this question on reddit but I can't find it. Do you have a link to that question on reddit?