Since this was bumped up, thought I would post my thoughts!
I have 2 German Shepherds. Now that we are empty-nesters, we are looking forward to vacationing with our dogs, but it is really getting hard to find hotels that will take two dogs over 50 pounds! Especially ones where I can use my hotel points!
Also, finding a vehicle that will comfortably hold 2 cages for GSDs is not easy. I thought I would go down to a smaller vehicle once my children grew up and there were no more car pools for tuba players and such, but no, now I need even more room. The $68,000, fully loaded Toyota Sequoia looks good, but the fact that it costs almost what our first house did is giving us pause!
Before we got our second Shepherd, we had taken our other dog from Northern IL to Florida. We spent a few days in a rental on Cape San Blas, FL, a very dog friendly place on the Panhandle. Here, your dog can run free, and play in the ocean with you, and go on fun explorations! We have not found this to be the case at many other beaches, as most do not allow dogs. People still take them, but it is at your own risk. I prefer places where I know my dog is welcome, not a place where people make snide remarks even if my dog is leashed and walking next to me. I highly recommend Cape San Blas!
We have also taken our dog to Disney, but kept her at the Disney kennel (Best Friends, I believe?). We would take time to visit with her during the day, and it was a nice break. I felt she was treated well while there, and I would not hesitate to use them again.
When we travel, I like having the cage in the car so the dog can stay in it, but I don't close it as there are only about 4 extra inches beyond it. This way, she can have a little space to stretch out more. With two dogs, we have not yet gone on long trips, but we have gone to Starved Rock and out to visit our DD in Indiana. We don't have room for the two cages, which bothers me, but we put the seats up in our SUV so if something happens, they have some sort of barrier.
Do keep in mind that most hotels will not accept you with your dog unless you have cages to keep them in when you are out of the room. Also, ask if they have a sign to put on the door so housekeeping does not come in unaware that you have a dog (especially a big dog that is super friendly and wants to give a good kiss, but all housekeeping sees is a big furry beast with huge paws and big teeth!

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One more thing, I do find that having my dog on a short lead attached to her collar in the car is good in case there is an accident and the dog gets out, but when we stop for walks, I put on the retractable leash as my dogs are used to going away from us to do their business. They don't pee on walks here at home, as we have a huge fenced in yard for them to relieve themselves, so it takes a few times to remind them it is ok to pee while on a leash, but it is so much easier if they have that 16' of lead for "privacy". At least, for my female Shepherd: my male lets it go whenever he feels like the spot is good, the more people to see the better, and if he can make the pee spray take over at least a 2 foot area, even better! He is really such a boy!
Have fun, it really is a pleasure to travel with the furry family members!