The "best deal" can mean the cheapest available thing or the best thing for an affordable price. I am 21 years old now and since being 18, I have travelled on my own, all around North America, parts of Europe, Dubai and South East Asia (Thailand, Singapore and Bali).
I consider myself pretty good at finding the best deal. I swear by Booking.com, of which I have an additional 10 percent discount because I have used it more than five times. With "booking.com" the hotels may seem cheap already. However I utilise the “No Prepayment, Free Cancellation” option and book, cancel and rebook (sometimes with the same hotel), all to get it cheaper and cheaper. I always look on "Booking.com" and research the different areas of a location.
In Dubai, I booked an apartment suite through "Booking.com" for £550 for two weeks! It was in “Internet City,” a business area with lots of hotels and centrally located.
The best tips that I could give for booking hotels and finding the best deals is to bulk book and book a choice of around five or six which is what I do for all fully planned parts of my trips (if you are travelling around and haven’t planned everywhere you are going, then just book the cheapest place). When I bulk book hotels I usually look at the facilities and location, and then wait to see which ones drops their price further.
Also with the location, do some research where you are going and the types of districts are in the location; for example business districts usually are the cheapest but quietest places. You will find areas to fit your needs ie: Partying, exploring, relaxing, or all of the above.
Time of year plays a part in cost of the hotels—which in Dubai is late August-December, and Asia is the rainy season (It doesn’t actually rain that much, maybe around 30 minutes on occasions).
Getting the best Flight deal can be a bit more tricky. You have to gamble and rely on certain times before the actual flight. Two to three weeks before can be really expensive with few seats left (on popular routes like Dubai/ NYC). However if you look early enough, two to three months before, and stalk the prices, then you can find a good deal. Websites like “kayak.com” tell you they have an algorithm to see when to buy. However I just go with my gut. I use “cheapflights.com” for all my flights. They do one-way, return or multi city, which I used in Asia. I could always choose the cheapest flights but if I travel with my girlfriend I would choose based on comfort as well, which is why I fly with Emirates and pay slightly more than some other airlines.
Other people may say to use the company's own website or a different comparison website; however cheapflights.com has never failed me. Even my nana and grandad are using "booking.com" and "cheapflights.com" instead of high street travel agents or package deals.
The best thing about booking separately is you can choose to splash out a bit more on the flights and fly with more premium airlines, or even upgrade your class on the flight, but then you can cut back and save on the hotels. The same goes both ways; for example, if you want a posh hotel you can book the cheapest flight available. I personally don’t care for hotels. I'd sleep anywhere as long as it was dry and had a comfy bed, but most importantly I want to be comfortable in a nice environment when I am flying seven or eight hours at a time in a tin tube, 35000 feet in the air.