Usually you can get a higher quality service for a better price than chains.
One tip, though, is to barter - especially if you're travelling midweek. I've got some excellent deals (including free evening meals, room upgrades etc.) by bartering at short notice for rooms that otherwise the hotel wouldn't fill.
The best deal I got was a full suite, several free drinks, and free breakfast at a 5* London hotel for the price of one of their basic rooms.
You just need the balls to negotiate :D
Never book online if you can avoid it!
Plus, they'd book all our reservations for us. We just cancelled the weeks we didn't need as we went.
Anyway, as a lark we decided to compare Expedia, at least, against the website of the hotel that we always would stay at and we were really surprised to find that it was actually cheaper on their website than on Expedia. And like you say, you get the bonus of loyalty points.
Hotwire may have been cheaper, but normally we found that booking through the hotel you would get Wifi and sometimes parking included, as opposed to paying for them separately and those things always evened everything out.
The only time I found this not to be true was when we were booking the hotel on the day that we were planning on staying there... that kind of timeframe has always been cheaper to book through Expedia etc.
I search the postal code of the place I want to be in the city (a combination of work location, downtown, neat area of city, near transit, etc.). Then I use the map to zoom on the area.
I filter by price and review. Usually find a well priced, beautiful booking with a good location within 2-3 minutes. Then I contact the host.
To me booking.com is the amazon.com of hotel reservations: you know that you're going to be served perfectly, in a timely manner, at a great price (maybe not the absolute best price you can get, but usually very close).
I once booked a three-day stay at a hotel in Portugal in the middle of summer. I missed my flight because the train was delayed (in France you don't have a choice for trains so it's impossible to not use SNCF, but I sure promised myself to NEVER fly with Air France again!!)
I called booking.com and they managed to move the reservation (the hotel was full but they were still able to do it) and they called me back right when this was done.
The contrast between this level of customer care vs. what we got out of Air France (in short: "tough luck / fuck off") was staggering.
booking.com never disappointed me.
or the hotel's website if I've been there before (and they have a booking page).
Google really has too many services for their minimalistic UI these days...
Their problem, as always, is they have no way to organize their interface. Google just simply (lol) isn't that good at UI design.
The other thing I do that is kind of risky is just rock up to a hotel on the day and try to get a good rate at the front desk. I'm at the Scottish Ruby Conference now and managed to get one of the best class of room here for less than my friend paid for his standard room. As a more extreme example last summer I turned up at the Ace Hotel in NYC hoping to lay my head down in one of their entry rooms for the night. Unfortunately they were fully booked except for the lofts which were ~$1500/night, there was no way I was prepared to pay that, and I talked them down to under $400. I called my friends and some girls and had a massive "house party" in my loft room. It was awesome! (pic - http://instagram.com/p/OdJmamMw2D/)
From the hotel perspective an empty room does not make them any money, they may as well have occupied even if it is deeply discounted.
Drinks. The table needs to have some bottle service happening.
I believe this functionality has been completely rolled out in the mobile (iPhone/Android) app if you want to check it out.
(Disclosure: I work for TA, but in a different department. However, I was a TA user before I joined the company, and continue to be one)
Also try http://www.hotwire.com for better deals
Case in point: lost my flight (because of airport issues), this was a sunday evening, so no one at the airport to help you book a hotel.
Grab my phone, booking.com, search for hotels at that airport, ok fee, etc, gets a taxi there
Night of sleep saved.
I also use hotels.com, which is nice for its 10th or 11th night free stay in participating hotels.
If I can’t find a coupon, I research the hotels and prices on booking.com and then call the hotel to negotiate a lower price by booking directly.
If I'm paying for myself I check hotel aggregation websites, and check prices directly with hotels I've stayed at before or that have been recommended to me.
Seems kinda barbaric but search sites don't list all the hotels. (Google does a little better, street view also helps)
Don't like chains as I find they have poor food and service.
They also do great cashback on Quidco regularly, and have their own loyalty program, so it's usually a great deal to go through them.