Cheating a bit, but probably two in Cuba when we were travelling around the country. Clearly as part of the 'tour' we were forced to stay in a combination of state run hotels (awful) and some private enterprises (lovely). The best was a private room in an old couple's house. They were so lovely, not a word of English but made great eggs every morning and coffee so strong it was like syrup
This was not too bad, it was a hotel we stayed in after a 4-5hr drive up to the Sierra Mountains where we had a ludicrously early start the next morning to trek through the mountains up to Fidel Castro's hideout. (Which was awesome!). The first pic makes it look ok as they were little chalets. But when we turned up in the evening, bearing in mind we were a good few hours drive from anywhere like even a town (there's not many restaurants in rural Cuba either even if we'd gone to a town..), they were supposed to feed us but had sent all the staff home. So we hung around your cliche of an empty dilapidated pool covered in leaves/dirt, with only half a bar, no staff, until they managed to get 'someone' back to cook what was actually a god-awful meal of stringy beef strips and rice. And remind them they were feeding us breakfast at 6am the next morning
Outside not so bad, quite relaxing actually, annoyed I didn't get a pic of the pool area because that was comedy;
Each chalet had two of these tiny bedrooms (that is the whole room pictured) with a shared bathroom. The A/C worked, but was too noisy above your head to leave on. Our neighbour's next door A/C unit fell off the wall in the night
But that one was quite fun because of the adventure. Below is one of the state-run hotels we had to stay in. Fortunately we turned up late, slept, and left. The door to the room didn't shut properly and had slats you could see through, a window pane was missing (next to the A/C unit), the shower had no head and dribbled brown water, and you could hear everything going on next door either in the bathroom or bedroom. To top it off, when we were leaving they held us all in reception for about an hour because they wanted to check we hadn't stolen anything. Like the towels, which were barely bigger than a flannel
Oh, that was the only light in the room that worked too (I think including the bathroom). But they left us a nice plastic flask to use (shown in pic)