Should I book ahead?
How far in advance do you need to reserve a hotel room?
Should you book all your hotels ahead of time to be sure you get exactly what you (think) you want? Or should you wing it and wait to find a place to stay until you actually roll into town.
Both. Neither. (I know: I'm a big help; it'll all make sense shortly.)
Below is my advice, but first ponder this: Until you're actually in the room, you won't know whether it's got a view of the castle...or of the sewage processing plant across the street.
My rule: Always reserve at least the first night's room—especially if you’re arriving on a weekend—but reconsider that tactic if you are booking the room for the whole first week.
To reserve or not to reserve, that is the question
There are three types of travelers, and I have different advice for each:
Type one: You're happiest making an itinerary and sticking to it, and you want to be sure you get the absolute perfect room every night.
Advice: Go ahead and book rooms for the entire trip now. Seriously. You'll feel better for it.
Type two: You prefer to play it loose and go with the flow. You have a plan but not a set itinerary, and want to be free to chuck your plans out the window in order to stick around a favorite town longer (or cut out once you realize you're bored), hang out an extra day or two to catch a festival, or just follow that cute guy/girl you just met wherever he/she is going.
Advice: Don't book too many hotels ahead of time. It will cramp your style and make you wistful for all the missed opportunities of spontaneity (and possibly trip you up with possible bad choices). However, I do recommend that you at least reserve the first night(s), then wing it from there. I'd also book a room for the last night as well, because I know that when I'm pulling into London (or wherever) on the final day of a long, tiring trip and know I still have to repack everything for the flight the next day and get up way too early to get to the airport, the last thing I want to have to do is hunt for a hotel.
Type three (most folks): You're like most people and fall somewhere between the first two types. You truly want to explore, but are also nervous about leaving too much to chance. You have a planned itinerary, but are willing to alter it if some great opportunity comes along (or you discover that the bits of England you are truly enjoying are not the bits you expected).
Advice: Again, reserve at least your first and last nights, plus hotels for any time you plan to spend in the major cities (like London), since the great, cheap, central places sell out fast in those towns. However, give yourself some leeway and leave things open for the rest of your trip, those days you plan to spend exploring the Cotswolds or Lake District, or hitting the less famous cities. I find peace of mind calling ahead (or booking online) from one city to the next a day or two in advance, but have rarely had any trouble simply searching out a room by phone from the train station upon arrival. (More on all this in the "Hotel Hunting Tips" section.)
Look into whether your plans happen to land you in a town on a festival day, in which case you're probably in for the highlight of your trip, but should reserve rooms immediately, from your home country, as far in advance as possible.
Same goes for trade fairs (not the trip highlight bit, but definitely the advice about booking ahead).