Booking Guidance

I prefer to book my flights directly through the airlines. Sometimes flight times are changed to something that wouldn't work, and for things like that I would rather be dealing directly with the airline than with a third party site. I will use kayak and like sites to get an idea of airfares, but I usually find the same fare, or close to it directly with the airline. For hotels I will book directly through the hotel when they have an easy process for it. When they don't, I have used booking.com without any issues.

I book directly with the hotel (either phone or email) I find that the prices are better than you see on a site like booking.com etc.

This seems to work better when you are going to be staying in one city or country, although I have seen Expedia now including an option where you can say you only need the hotel for a specific amount of time in the city you flew into. Sometimes you can get a good package deal.

My last trip May 10-17 2017, I booked a flight Chicago to Amsterdam via Detroit on Delta through Expedia that was $250 dollars cheaper than if I had booked it directly with Delta or any other airline (I did a lot of research); sometimes you get lucky
In my case it depends on the itinerary. I use Booking.com a lot for mom pop hotels that don't have their own websites otherwise I book directly with the hotel; but they must of just merged with kayak to sell flights which I never use.

You are going to half to research compare the costs of both methods

We almost always book flights directly with the airlines.
For hotels abroad, we use booking.com.

We almost always book flights directly with the airlines, although we use skyscanner to search options.
For hotels abroad, we use booking.com.

I do single-city, shorter (up to a week) trips. I have tended to research flights across airlines using Hipmunk.com, but then book directly with the airline. I always seem to end up flying with the airline of the country I'm going to (ie, Air France to Paris, Air Berlin to Berlin, Aer Lingus to Dublin, etc.) One advantage is it helps me feel "on vacation" a little sooner. I get to practice my crappy French before I've even left New York! Second, I always manage to find a good price--is it possible that these airlines are partly subsidized to bring tourists to the capital city?

However, this trip I happened to be checking prices and managed to get a really good price break on an economy flight and a pension-type hotel together for less than the flight alone would be if I booked directly through the airline. The price I got was for a rock-bottom room with a shared bathroom, but after thinking about that, I contacted the hotel directly and got an upgrade on my room to an en suite single. I've also put in a bid to upgrade to business class for the red-eye over--I'd really like to get some sleep! But even if that upgrade doesn't come through, I still have room + flight for less than flight alone.

kayak.com is always on the list for my flight searches, but it's not the only place I look. Like most of my planning, I start with fairly exhaustive searches of both search sites and airlines, set up multiple fare alerts for different options, then watch prices for awhile before I book.

One thing I'd highly recommend is to keep your dates flexible until you book your flight. It's easy to save a hundred dollars per ticket by moving a couple days one way or the other, sometimes you can save more than that. My last two (and next flight in September) round trips from DC have all been under $500, NY to Paris is even cheaper.

I book lodging seperately. I've used booking.com many times and never had an issue with my reservations. I do have a beef with booking.com on one of my reviews from May. I stayed in Beune at a hotel that was rated "good". It was awful. The bed and linens needed to be replaced decades ago but the worst was they had no hot water. I asked the owner, thinking he forgot to turn on my hot water and he said that was as good as it got. He had a bar/restaurant too, no telling how he got his dishes clean. I rated the hotel bad on everything but location and booking.com gave the hotel a "good" rating - and wouldn't let me revise it. Now I think sleeping in my car near the center would be considered good accomodation by booking.com.

I'm thinking Europeans use Tripadvisor often to book rooms (and find restaurants) when traveling.

While I use a travel search engine to find fares and flights (often Hipmunk), I always book the flights directly with the airline. On the other hand, for hotel rooms I use booking.com sometimes and other times directly with the hotel. For example, on our recent trip, for the 2 hotel nights I reserved by email directly with the hotels, neither of which asked for credit card info. One of them was on booking.com and one wasn't, and I would have used booking.com with the one if they hadn't responded to my email. I've never had an issue with a booking.com reservation.

For our trip to Italy in May I had put off reserving most hotels until early April, then did a marathon session with booking.com and got rooms in six cities in six hours -- all of them turned out fine, several are now on our "go back to this one" list. (And one is on the "make a special trip for this" list.) Had booked airlines separately when KLM was running a big sale months earlier.
Doing a one-location trip, there can be some great air-and-hotel packages.

I always book hotels through the hotel's own website. Relatively few rooms are released to brokers and I don't find the prices to be compelling compared to the hotel's prices on their own website.

For the last few years I've been booking hotel/air package deals. I only fly Delta or Air France to France, and in the last two years I have paid very little for the hotel. Priceline and Expedia and many of the others allow you to use your frequent flyer numbers, and when you record that you can check it on the airline's page and make changes accordingly. The last few times the airline charged me directly through either Priceline or Expedia.

To give you an example of my most recent deal, I'm spending Christmas in Lille (10 days). I only paid $1001 for a direct flight to CDG and then I hop the TGV to Lille from CDG2. It included direct flight to CDG from ATL, TGV ticket, and 3-star hotel for 10 nights. If I were to have booked the flight alone with Air France it would have cost me $1302 - $301 more dollars than booking the package deal. How does that work? Not sure. I did the same thing last year and stayed at a beautiful Mercure hotel in Paris and only ended up paying $200 over what the flight was alone for both hotel and airfare.

That said, I usually travel over the Christmas holiday (when rooms aren't always full) and I always plan about 7 months ahead of time. Seems like many hotels offer excellent non-refundable rates. I usually then opt for the 30-40$ insurance just in case.

I used to book separately to wait for hotel deals, but I no longer do that. I just make sure I've researched the hotel well. Hope this helps!