If they're related to poicephalus, why do they have a bare eye ring? I've always wondered. It seems more macaw or conure like, yet, there they are.
I don't have a Jardine's, but I do have a red-bellied parrot, which is another member of the Poicephalus family. Also worked with senegals and meyer's in the past. It's less obvious on them, but they do all have a bare eye ring. It's just dark enough that it blends well with their feathers.
To answer your other question, just in general it depends on the individual bird. My flock are all good with travel, but they're also very used to being in the car. I take them with me to the bank, stores that allow them, the beach, parks, and (prior to covid) street fairs/festivals. I do this largely in part so the two-hour drive to the vet is less unusual and stressful for them. My starling has been on four separate day-long road trips because his care is specialized enough I'm not comfortable leaving him with a sitter.
Just make it a normal, fun thing and I believe he'll adjust fine to visiting the cottage. However, keep in mind that some birds do get carsick.