Just curious: if puppy is used to sleeping in your bedroom (either in crate or next to/on the bed), how is your experience with pet sitters or holidays?

My puppy (7.5 mo) had a hard time sleeping alone in his crate, so I decided to keep him up in my room and I have managed to get him to sleep very well now, with me in the room, but not directly in his line of sight. In the morning, he tentatively whines me awake around 7 and I let him on the bed for some morning cuddles (which is 5 mins on working days or +1 hour on home office/weekend days). As this is working well and the good sleep quality has finally helped me through puppy blues, I have no intent to change this anytime soon.

I have a work trip coming up and my mom is going to look after my puppy and sleep in my room while I am away. But I am wondering what to do if she can't sit for my next trip or if I want to take my puppy with me for a summer holiday. For people in similar situations, how are your puppies/dogs dealing with being in holiday homes/hotels or sitters (either in your home or their own) dealing with your nighttime habits?