I've only ever been on one holiday with a friend and will NEVER do it again!
Myself, DH and DS had booked two weeks in a caravan abroad. Friend expressed interest in going to said destination so we invited to stay with us for free, as long as she booked her own travel and contributed to meals and food in the caravan etc. She decided to come for a week in the middle of our two week holiday. All was fine and I was eager for her to join- we thought it would be a nice opportunity to have a date night as she had previously babysat for us and DS was very familiar with her.
She arrived, and all was well for two days until she suddenly stopped pitching in for meals etc. She expected us to pay for buses/ trains/ drinks EVERYTHING. I brought it up as diplomatically as I could and she later brought me €20 to contribute (we estimated she'd cost us around €100!!!)
We let that slide as we didn't want to cause upset.... Then she really started to piss me off. She started completely ignoring me and spent most of her time talking to my (now) husband. Back in the caravan she would literally get in from a meal with us and go to bed! Obviously she is well in her rights to do so, but we thought it was a little rude to do this every night without even saying goodnight!
DH and said 'friend' went to the local water park one day (I'm not a fan and our son was too young to be able to justify his entry fee.) said they'd be back by a certain time, so I made an effort to prepare a nice dinner and get some wine etc in. The time they were due home came and went- I ended up having to put DS to bed it was getting on so late! Eventually they turn up, pissed and with an empty churro cone. I FUCKING LOVE CHURROS. And they didn't save me any!!!
The last thing to really piss me off: DH convinced me I was getting angry over nothing, so I made a massive effort to find a nice place for breakfast on her last day, and booked us a table. The time comes around for us to be making a move and she tells me that she wants to go straight to the airport instead. Didn't see the point in taking DS all the way to the airport if we weren't doing anything special, so we stayed behind whole DH escorted her to airport. When he comes back, I ask him if he's eaten and the little fucking bitch had taken him for breakfast in a fancy restaurant!!! I couldn't speak to DH for the rest of the day as I was so angry.
(DH is on the austistic spectrum, so completely misunderstood why I was so angry!)
When we all return, I meet with another friend who tells me the girl who came on holiday with us said my DH came on to her the whole time and made her pay for everything!) after about months we manage to salvage out friendship. Until she's my bridesmaid and really fucks things up (that's a whole other story!)
So yeah... Never holidaying with friends ever again!!