Singapore's Major School holiday is June and November/December, so during this two period where you can come to Singapore for bargain, especially on June to August or September for the Great Singapore Sale. Singapore also has its X'mas Sales in December, but not as grand as the Great Singapore Sale. Airtickets to Singapore and hotel stays is usually cheaper in June to September period, due to wowing more visitors, except for the period in or near National Day (August).
As for Hong Kong, Winter time is the cheapest time to go to, as I always go there during Winter Season in Hong Kong. Hotels and airticket are usually cheaper in January till March in Hong Kong, due to lower influx of visitors to Hong Kong. Hong Kong sales season is usually July to September and December/January and sometimes into February (depends).
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