When I stay at a B&B or hotel I always inspect the room before unloading the car and taking my luggage to the room.
The contestants really have no idea about the activities they will be doing so need to be prepared for sporty outdoor stuff, possibly in the rain, as well as smarter clothes for the evening meal.
It is filmed over 10 days and they do go from one B&B to another, but not always. Of course they need to take extra clothes, it wouldn't do to appear on tv in a white shirt when wine or egg has dripped on it :D