As for Reservations with Long Ahead
1 - Whenever possible, rreserve Hotel + Flight
For starters, if you need to fly to reach your destination, choose to book them together. This solution will make the price of both have considerable discounts both for the advance and for the accumulation of products.
2 - Book As Soon As You Can
As a rule, hotel rooms are available 18 months in advance and flights 11 months. Do your math to try to understand if a reservation before 11 months is worth or not the fact that you are going to book only for a stay.
3 - Avoid Times and Days of Greatest Demand
If you have an option, choose intermediate weather times of the final destination you want to visit.
Avoid weekends when accommodation is substantially more expensive than on other days, with the exception of business and financial centers in destinations where hotels can have lower prices on weekends.
4 - Check if hotels launch promotional offers based on advance
As a rule, they appear between 20 days and a month with very strict booking conditions.
As for reservations with little advance notice
1- Hotel magic hour
On the day itself, the ideal time to find surprisingly pleasant prices is late afternoon.
Around six in the afternoon, most hotels release the vacancies of rooms they had kept reserved for group bookings.
If for some reason there was any cancellation of these reservations, all the rooms involved will almost certainly have low prices.
2- Trying to lower the price doesn't cost
If you are booking by phone directly to a reception desk or in front of that reception and it is already at night, ask if a lower price is possible.
No hotel or motel manager wants rooms empty for the night ahead, and for many it is better to sell them for a lower price than to leave them empty.
3 - No special discount, Net Price is Almost Certainly Lower
If you have Internet access or get access to the hotel's own network, compare the hotel's over-the-counter rate with the Internet rate.
The one on the Internet is almost guaranteed lower so, despite having already arrived, it will be worth it for you to go out and make your reservation right there, on a laptop, tablets ou smart phone.
Generally
Don't be dazzled by the number of stars
Stars do not always correspond to comfort and sophistication.
Instead of the number of stars, check carefully if the hotel or Bread & Breakfast you are booking for has the equipment, services and extras you are expecting. If it does, it won't matter if it's 4 or 5 stars as long as it's the least expensive.