Hotel and flight bundles

I've used Orbitz (but not Expedia) a few times for great deals on flights and many times for hotels, with no problems whatsoever. I did not find the same flight prices directly on the airline sites. I have often (but not always) found that hotels are less expensive when booked directly, or you get an additional perk by booking direct, such as breakfast when otherwise not included.

As long as you really like the bundle (both hotel AND flight) and you book with a reputable third-party like Expedia, I don't see any issue. I've had no problem with third parties (Expedia, Orbitz, Priceline, Hotwire, booking.com, etc.) but I haven't used them for bundled products. Just make sure the bundle, price, and itinerary is good and read all the small print. You likely won't find a very receptive audience on this forum for third parties due to habit, risk-aversion, "but Rick said....", etc. To be fair, there are pros and cons of the direct vs. third party approach. Do whatever's right for your budget and risk level. The only thing I wouldn't do is to book with some really obscure third party with no visible track record or reviews, etc. (I got burned once doing that, but luckily my credit card company came to the rescue).

I've used bundle and save many times with Expedia and never had a problem with that particular aspect of Expedia. I know the common advice I see on travel forums is that it is cheaper to book directly with the hotel and airline but that is not always the case.

There is never any absolutely. While it is common advice to book through the airline, sometimes it is cheaper elsewhere. We recently book two one-way tickets that were substantially cheaper than the exact same round trip ticket. Always check all options.

Airlines also offer flight/hotel bundles. Look at them as many include cancellation.

I often use British Airways for flight and hotel or flight and car hire bundles and they are always significantly cheaper than booking with the hotel/car hire direct.

Hotel wise, we have loyalty programs with several so we always get better rates booking direct.

I don't use Expedia after several concerning accounts I read about them refusing to help when problems have occurred with bookings made through them. I'm also a bit more wary of private rentals due to the slew of fraud occuring on sites such as Homeaway, Owners Direct etc. An interesting article from The Guardian on how the fraud is conducted:

https://www.theguardian.com/money/2014/aug/23/holiday-book-online-owners-direct-homeaway-scam

Those using third party, did you have better experiences when there wasn’t as much lead time. Since we are still working we have to book months in advance because my husband has to put for vacation in Janaury. We were thinking that when we retire and can look for trips, say, a few weeks out, the deals from expedia, orbitz, etc might be worth the risk. Does this make a difference?

When we went on a bundle trip last year (a week in Rome that was great), I increased my insurance to cancellation for any reason.

I have used Travelocity and Expedia several times for rt trips to Italy, when their prices are better than the actual airlines' prices. For example, I recently booked two weeks, in and out of Rome (from New Orleans) over the 2019-2020 Christmas/New Years holidays, on Expedia, bundled with a Rome hotel for 4 nights (decent hotel; good reviews on booking.com, good location). On Delta, United or American, the price for just the flight was approx. $2,000. With 4 nights in a Rome hotel, on Expedia, with Delta going over and Air France coming back, it's $1,350. When I used Expedia last year and had a problem with an airline-created time change in flights (several months after booking), Expedia easily rebooked me on a better connection when I called them and asked them to help with the problem.

I have also had good experiences with bundled deals on Expedia and Cheaptickets (owned by Expedia). I wouldn't hesitate to use any of the main brands like the 2 I've used or Travelocity, Orbitz, etc.

Just be careful when choosing these flights in the bundles. Stick to mainline carriers and make sure your layovers are long enough for customs, delays, etc. Also, make sure you understand which carriers include checked bags, carryons and who charges for seats.

For the hotels, I make sure I book exactly what kind of room, bed, view, etc. that I want and read lots and lots and lots of reviews.

In the peak travel times (late spring through early fall), I find the bundles save a ton. In slower times, booking directly seems to be better.

For example, July 2018, 3 of us flew to Rome on Air Canada through Toronto for 6 nights and had a small studio apartment (1 king, 2 twins) with private terrace and continental breakfast delivered to our door each morning in the Monti neighborhood for $1,400 pp booked through Expedia. We booked in late January/early February. At the time, the flight alone was well over $1,400 on its own. So, essentially we got the accommodations for free.

On the other hand, in January 2019, 5 of us flew to Paris on United through Chicago for just over $500 pp. We booked directly on the United website in October. We stayed in the 5th in Paris in a lovely hotel I'd stayed in previously with a wonderful breakfast included in 2 triple rooms (2 twins and 1 chair bed in each room) for ~$400 pp for 5 nights. We booked with the hotel directly on their website. In this case, the same bundle on Expedia came in at pretty much the same bundled price so there was no advantage there.

I also always get trip insurance!

I am headed back to France in October for a week - destination still TBD - and based on prices I see, we will most definitely book using a bundle. On Expedia's bundles, I see great flights on American through Charlotte with perfect layover times and depending on destination, bundles are coming in about $1,300 for 6 nights which is better than the flight prices themselves right now - ~$1,500 on American's website.