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Without flights two or three weeks before. For roadtrips we usually only book the first hotel and then decide along the way. For air travel we book 2 or 3 months in advance and then often also do roadtrips using rental cars booking only the first and last hotel in advance.
The only short vacations I really need to plan long time in advance are multiday bike trips where I want to take a bike on a high-speed train (because there are only few places and they are booked out super early). For example for a Bike-Tour from Innsbruck to lake Garda we had to book the train 5 months in advance.