Sri Lanka
The winter season for the South and SW coast - Hikkaduwa, Midigama is November to March. Beyond March and you get into the monsoon season which we had on a few evenings. Nothing drastic, just heavy rain for 30 mins or so but I guess it gets worse. The winds are more frequently onshore after March.
Finding accomodation is easy, room prices range from £1.50 per night for a basic (double bed, fan, shower & toilet) right on the beach to £30+ per night. There are hotels all along the main and only street in Hikkaduwa. 
We just turned up at the airport and shared a taxi with another couple with boards who were on the same flight. The taxi took about threee hours due to the traffic - unbelievable!
Bikes, mopeds, oxen carts and lorries = chaos! Once in Hikkaduwa we found accomodation within 10 mins and paid around £2.50 per night.
'My girlfriend now wife' upgraded our accomodation to a villa for between £5.50 and £7.00 per night including breakfast. It had a balcony overlooking the beach and was a two minute jog down to the beach or reef. Meals cost 50p! Taxis known as 'Tuk Tuks' will get you anywhere, for next to nothing.
After March there's surf on the East Coast at Arugam Bay but I didn't go there as the Tamel Tiger situation was a bit dodgy. There is a website for the surf shop at Hikkaduwa - search for surf/sri lanka and you should find it along with photos and accomodation above the shop which overlooks the main reef. The 'Lonely Planet' guide for Sri Lanka has alot of detail on Hikkaduwa, hotels and even surfing. It's definitely a very warm, mellow and cheap surf spot once you get there - Chris King
Read about Aran Pitter's 2003 trip to Arugam Bay
