Here, especially, it a question with a lot of meaning because where someone chooses to stay tells a lot about them. If they are staying at the RV park, well then they are professional travelers, they spend a lot of time on the road, but then again they might be staying here for quite some time. If they are staying in a condo at the beach, they are maybe dipping their toes in, maybe it is their first or second time here, still trying to decide if they like it; and they probably have some money. If they are staying in their own house, well then they are full-fledged snowbirds - six month types - that are engaged in both communities in which they live; here and some cold weather place in points north.
I wonder if John's disciples were looking for some coded information as they ask Jesus, "where are you staying?" To me, it seems less strange a question every year. Is he staying with family? Friends? On a mountain top somewhere? Behind the synagogue? Does he float up to heaven at night? Where Jesus is staying can tell us a lot about what he plans on doing. Sometimes he spent a while in a location, sometimes he just passed through. Sometimes he stopped to teach, sometimes people were healed just by touching his cloak as he passed by.
Maybe they were hoping Jesus could offer better accommodations than John. Whatever the reason, the question is worth considering. Where was Jesus staying? What does that tell us about what he is up to?