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We go to Myrtle Beach for vacation and we always book a week or two in advance while keeping an eye on the tropics. We can't afford to book a vacation that gets canceled by a hurricane.
Flights- book fairly far out. We don't have great budget airline coverae in my neck of the swamp and last minute deals are hard to come by.
Hotels- generally book a refundable reservation along with the flights. Will check a few times before departure to see if there is a cheaper/better option.
Rental cars- since the major companies a) don't even require a credit card to make a reservation, and b) seem to allow discounts and discount codes totally randomly, make one reservation as a placeholder and then recheck for something better maybe every 10-14 days. For our recent Colorado trip, the car reservation that finally stuck was one that was about 7 days out when I got a pretty good discount code from the La Quinta hotels e-mail list.
Only air tickets. I have a very strong resistance to ever booking anything in advance. There are very few times I could not find a suitable hotel within walking distance or local bus of wherever they kicked me out of the bus or airplane. You always find something, with little difficulty. And you get to look at it before you commit and pay, and walk away if it disappoints.
Nevertheless, I still call it "terminal anxiety", when the bus pulls into the terminal in a city I know nothing about in a country where I don't speak the language. If it's an airport, there is a whole planeload of people, lots going to hotels, and ways to get there.
If it's a popular destination, like Katmandu,there are touts hanging around who will take you by taxi to their hotel,quoting a guaranteed price, no obligation to stay there, and plenty more hotels nearby.
One of the best was when we arrived in China, the only foreigners on the river boat from Hong Kong, in Wuzhou. It was after dark, they stamped our passport, and everybody looked local, with no hotels in sight. A lovely young lady walked up and said "Hello, I'm Sherry. Are you planning on staying at the hotel recommended by Lonely Planet?" We said Sure and she escorted us through the dark and down a muddy embankment to a rickety motorboat ferrying passengers across the river to the city, walked us to what she recommended as a better hotel, got us checked into a comfortable affordable room, and asked if we wanted her to get us tickets for the morning bus to Guilin. She came back a half hour later with the tickets, we paid her for both the hotel and bus and a small gratuity for herself, and she showed us what looked like the only place in town still open to eat. With a lovely introduction like that, who needs reservations?
You are far more trusting of local touts than I am.
Edit: To the OP - I generally book 6 weeks to 5 months in advance. Usually (though not always), the best deals on flights and hotels are 1.5-3 months in advance. Last minute deals can be interesting, but I am wary of leaving myself at the mercy of events/availability.
It depends. Business trips are often less than a week's notice. Every now and then I hit on a good airfare and jet off to NY or LA for a weekend with only a few days notice.
I generally book international trips about 3-5 months in advance, and domestic trips maybe 2 months in advance.
This is how I usually do it too, although there have been a few trips I've booked up to nine months in advance because there was a sale.
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