The old chestnut "You all meet in a tavern," is rather scorned, with good reason. It has so much of the off-the-shelf fantasy world about it. The inn is, however, not just a place of meeting - but of rest. The intrepid band marches down into the dungeon and troops back later in the day short on or covered in blood and treasure. They sharpen swords, read spellbooks, make a hasty meal - and go to sleep.
What sleeping arrangements does the inn offer? A crowded bunkroom with the other cowhands? Seven feet of space in the hayloft? Sharing a bed with a strange giant and a strange doctor? Individual rooms, with bedside tables and alarm calls in the morning?
This last one would be the answer of the less than inventive setting. A quick look at the accommodation in Skyrim, for instance, rather makes me think of a Norse-themed hotel, devotedly recreating mead and roast boar and smoky longhouses, but then letting you trot off to your own cosy bed, in a private room, complete with ornate knotwork-patterned eiderdown.
(My quiet scorn for this kind of fantasy is lifted in a setting like Modesitt's Saga of Recluce - where the entire thing derives from crashed astronauts, hence the insistence on handwashing amidst the swordplay and fireballs, and why the quiet feeling of things being all faintly a little like a Western has some justification as an attempt at a modern society with limited resources. I cannot recall quite whether Anne McCaffrey's Pern was the same; I have more memories of dormitories.)
Speaking of Westerns, this has some convenience to it; if Our Heroes are passing through a one-horse town, just saying 'You all find rooms at the local tavern, a charming establishment called The Owlbear's Head' is not perhaps unreasonable. It might be tempting to mix this up, occasionally: 'Old Man Johnson will let you sleep in his barn for a copper penny a night. No open fires and you have to find your own food, but well water is free.' Naturally, this would be a really small town.
This question has more interest when we go to the big city and if we factor in wider associations. That is to say, Peregrine the Paladin might get lodging at the Chapterhouse of the Order of St. Tankred, but said Order might not care for the freeloaders in his wake - who, as ever, might be heretics, infidels, wanted by the authorities, warlocks or the like. Likewise, Clothilde the Cleric might find an empty bed at the local Vicarage equivalent but then violently disagree with the Vicar on a thorny theological issue.
It is tempting, further, to imagine a trip to the city as an opportunity for Our Heroes to get some time to themselves; the Wizard consults her colleagues in the Occult College, the Elf gets to enjoy the comforts of superior Elven company. They then meet at a pre-arranged time to continue the quest. Perhaps this has always been part of the rhythm of play; finish the dungeon, level up, go and find someone to teach you that neat sword trick where you flip the blade out of their hand. If so, perhaps the change in atmosphere could be better communicated. 'Peregrine, the sound of evensong in the Chapterhouse of the Order is heartening and comforting after so many nights spent camping in the ruins of the Dread Bastion.'
All this aside, however, I would raise another question. What sort of society offers large sets of rooms in relatively commonplace guesthouses? That is to say, the equivalent of The Blue Boar or The Owlbear's Head offers its most thrifty guests staterooms and private bathrooms as a matter of course.
One imagines a world with a lot of space to spare - the diametric opposite of the capsule hotels of Japanese cities (another flavourful way of communicating setting) - and, moreover, relatively cheap labour to build the sort of hostelry that can offer the humble wayfarer the equivalent of a luxury suite. An image from science fiction might call to mind architectural nanobots, able to construct a palace in seconds - the idea of luxury in such a place comes from the manner and skill with which it is decorated and furnished, rather than the possibility of having five rooms of one's own.
The vast worlds (and habitats) and vast resources of the late Iain M. Banks's Culture series might suggest themselves. Robert Silverberg's Majipoor, or something like it, seems as if it might offer something similar. Majipoor is a vaster planet than Earth, and the somewhat sumptuous tones of that series (or an imitator) conjure a world where such a thing might be possible, or indeed expected.
What other images could we suggest for a world of vast houses? A tent city of the desert, where a new wing is only a matter of new poles and canvas, but where water is infinitely precious? An off-world colony, where many more thousands of prefabricated housing units have been provided than are needed? (Not just replicant servants, but many more square feet of housing than 2019 Los Angeles offers).
Is this phenomenon rather socially developed? Has this polity developed curious luxuriant and stringently enforced housing laws? Does tradition demand different wings of the house for the sexes? Does a divine command call for a private space in which the faithful may make their prayers alone and uninterrupted?
Further suggestions in the comments, if you've something to offer.