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I'm an older guy who's traveled globally most of my life, but I am about to take my first real vacation ever and just realized that I have never traveled outside of the military and business settings where someone else had the cumbersome task of choosing flights, hotels, etc. Now that I am forced to do this myself, I'm finding the travel industry very peculiar, almost scam-like.

I avoid Expedia due to their past failures on business trips, and Booking.com has prices much higher than the airlines indicate, along with sketchy cancellation policies. I don't have any intention of canceling, but we all remember COVID, and emergencies can happen, making cancellation and travel insurance a comforting thing to have.

Can anyone provide me with sites/companies that are honest and not playing the bait-and-switch to get the most money from the customer? I'm not traveling for three months but want to purchase my flight and hotel now in hopes of getting a better price. Where do I start?

David
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In general, you should always book directly: on the airline's official site for flights, on the hotel's official site for hotels. This way:

  1. you get the best prices (many brands even offer a guarantee that you can't find lower prices elsewhere)
  2. you can avoid out-and-out scams, since a (say) Marriott hotel listed on the official Marriott.com website is pretty much guaranteed to be the actual hotel
  3. making changes/cancellations or dealing with problem is straightforward, since your contract is directly with the provider
  4. you get frequent flyer miles/hotel points

You should, however, comparison shop before committing to an airline or hotel. The more options you have for dates, routes and destinations, the lower the prices. Reliable options for flights include Google Flights and Skyscanner, while for hotels I often use Booking.com for searching (but rarely actually booking).

Also, since I'm sure this will be pointed out in the comments, these are generalizations: particularly for smaller properties it's not uncommon to get better prices or conditions (free cancellation etc) from Booking or other third-party sites, and on rare occasions a third-party flight booking service will have better prices too. But if you want to minimize risk, booking direct is always the way to go.

lambshaanxy
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The third bullet point of lambshanxy's Answer reduces triangulation in case of problems, and is the most significant benefit for the traveler. The lower price quoted by online travel agencies et al is rarely worth the agony of being caught between two other parties if something goes wrong: for instance, the online travel agent who says it's the airlines' fault and the airline itself, who will always maintain it's the online travel agent's fault. This is not a happy place for the aggrieved traveler.

DavidRecallsMonica
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I've generally had good luck with Booking.com and Trip.com in Asia and Europe. Expedia and Agoda less so. Airbnb can be useful in some cases, but more rarely these days. Skyscanner and Google are useful.

Pricing aside (you have to shop around and I agree you should check the hotel directly) some of the websites are better than others for showing you the area hotels are in (unfortunately you still have to go to Google or Apple maps with the address usually) . One of the things I spend some time on is looking at when flights arrive and leave and how I will get to and from the airport (free shuttle?) and wherever else I am going. Is there a metro line? An express bus into town? What hours does it run? If you've not got a tight budget and are just going to grab a taxi it doesn't matter as much, but even spendthrifts might gulp a bit at taking a taxi solo to NRT, IST or HKG from a far-flung hotel. And if you arrive too late you may get stuck with paying for an expensive room just to be able to travel the next morning when the border opens or whatever.

If you have a local (as in local to your country) deal finding website for flights they may be useful when airlines are practically giving a limited number of flights away. If you're flexible that can be a great way to reduce costs. Personally I have a spreadsheet of places to cross off and if a deal comes along that fits, I will try to grab it. I'm not sure subscription services are worth it, in my area the sites are ad-supported and therefore free to use.

All this is actually work, and takes significant time and effort that your assistant was doing (or not doing). On top of that, it's quite unlikely you'll get it perfect on the first trip to a new place. But you'll probably be close enough to roll with the punches and enjoy the trip.

Occasionally, you can get a routing or a price that's substantially cheaper by going through a 3rd party. I've used that and it's turned out well, but I won't for a $20 or $30 difference. For $200+ and a 3rd party I know, yes. Some of the dodgier sites have additional charges that eat away any difference anyway.

Depending on where you live, booking with a local website may give you additional consumer protections (such as free 24 hour cancellation of flights). On the other hand, sometimes you can book with the foreign website (of, say, an airline) and get a better price after currency conversion. That seems to be true with some flights to Central or South America.

Spehro 'speff' Pefhany
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Skyscanner.net is good for flights. Once you choose a flight, the next step offers to transfer you to the airline's website and also to a selection of third party booking agencies. Beware that if your ticket has more than one leg (including outward and return as a two-leg ticket), many airlines will cancel the remaining legs (without refund!) if you don't use the first leg.

Booking.com often has cheaper deals than the hotel itself offers. We recently booked a room for €64 that the hotel was asking €120 for.

reallydismayed
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It is best to use search engines that compare prices between travel agencies and airlines websites.

You might want to try Trabber.com or Momondo. They are reliable site for comparing flight and hotel prices. Plus, sometimes they offer discount codes in the results, which could help you save even more.

danzar
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I avoid Expedia due to their past failures on business trips, and Booking.com has prices much higher than the airlines indicate, along with sketchy cancellation policies. I don't have any intention of canceling, but we all remember COVID, and emergencies can happen, making cancellation and travel insurance a comforting thing to have.

Not sure which "failures" you're talking about. Cancellations and everything in many cases are covered by your credit card insurance, so doesn't matter where you book.

Of course if you have extra $$$, you can book directly (both air tickets and hotels), but I strongly recommend not to, at least, not in the first place.

  • For air flights, I find skyscanner being almost the best, you cannot buy tickets there as it's kind of "aggregator" service, but instead if provides overview of different sales points and their prices, so you can see how is the price different on airline website vs on booking vs on random website like trip/mytrip/gotogate (I had booked tickets and flown afterwards on all of them, nothing "sketchy" there btw). If the price directly on airline website is not so much different - in this case go book there. Otherwise doesn't matter really.
  • For hotel reservations, booking-com is the best hands down. Also airbnb if you're considering apartments/houses, but in most of the cases booking is good enough.
okainov
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