It depends very much on the chemistry you want to use it for. What sort of stuff are you having in mind?
If it is for normal, "stoichiometrically moisture sensitive" reagents, e.g most hydride reagents or simple grignard chemistry, it may probably stay dry enough for weeks and weeks, particularly if you use proper schlenck-techniques when handling it. For this type of chemistry, many people don't even bother to dry the THF, just make sure your bottle is reasonably fresh (weeks to months). Of course, it depends also A LOT on the air humitity where you live.
On the other hand, If you are doing something that is on the very extreme, like eg something with a minute amount of a highly sensitive catalyst, you might not want to store it even overnight. Maybe store over molecular sieves?
If you don't have access to a continous dry distilling apparatus, I would not reccomend putting up one for occasional batchwise drying. Maybe you can get by with using molecular sieves, or buying dried THF when you need?