For reservations it depends on the class of hotel -- for the cheap backpacker options, you'll find it cheapest just to show up, but for mid-range and above, take a look around on the never-ending spply of hotel-booking-websites -- some have very low rates.
For hiking boots, i'd go with heavy-duty sandals rather than boots -- not so hot on the feet.
#2 somtam2000 has been a member since 21/1/2004. Location: Indonesia. Posts: 7,770
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I've just left Chiang Mai after having spent around five weeks there, on and off. Now, the tourist season there is over, and you'll have no trouble finding a room, and little trouble negotiating for an off-season rate.
I stayed at the Parasol Inn (http://www.parasolinn.com), a new hotel/guesthouse slap-bang-wallop in the middle of the old city - literally at the centre. It has TV/AC (it's VERY hot there now), clean and comfortable rooms, nice staff, you should be able to get between 400 and 600 night for a twin/double. Rooms 2, 3 and 4 01,03 have a view of Wat Chedi Luang from the bathroom window - the bedroom windows are internal to the bathroom. On a Sunday, Chiang Mai's famous walking market is literally on your doorstep.
If you go to the hotel, negotiate down by saying you don't want the free breakfast - food isn't their strong point right now.
I loved staying there, was on first name terms by the time I left, and I couldn't recommend it highly enough.
Somtam's right about the hiking boots - too heavy. But I'd avoid sandals if you're hiking near waterfalls (hopefully you will be!) - the rains have started and there are a lot of leeches around. Get decent lightweight but robust shoes and mesh socks - these will offer you some protection.
Have a fantastic time!
#3 totallygone has been a member since 6/5/2006. Posts: 6