I generally also bring just one handbag and use it. However if I end up buying a luxury item then I would lock it in the suitcase. You should choose a hotel which you would feel safe to stay in the first place. If you can't trust a place with your locked suitcase then you probably shouldn't stay there.
I usually bring one Mini and one WOC. Bring them in dust bags and a large ziploc bag for each. Usually both can fit in room safe at same time plus Ipad, camera, etc. I bought a Hermes bag in St. Bart's this past December and hid the bag in the closet behind hanging clothes. Nervous even though we were at 5* resort.
I take my Chanel bags on vacation with me everywhere and have never had a problem...I will admit I only stay in 5 star hotels and I leave the do not disturb on the door and also keep my bags out of sight though.
It never occurred to me that this would be a problem. I just took my Birkin, a WOC and a Prada cross body to Europe. I would use one and leave the others in the room. Maybe I am not suspicious enough, but the though of theft isn't even on my radar.
usually i put it in my carry-on, lock the carry on and then put the locked carry-on into my locked luggage, and store the luggage out of sight, like in the closet. i try not to take more than 1 bag though, but i use this system for any valuables i have to leave in the room or any souvenirs i buy
This is a tough question. Las Vegas is where I have the highest tendency to buy a high end item. Sometimes they fit into the safe...sometimes not. I take with me & carry a low key LV in Damier Ebene (more under the radar) so I don't scream expensive items. I never wear high end jewelry either. My sister did and her room got broken into and she lost some of both her & our Mom's jewelry.
I try to buy very close to the end of our trip, then I lock it in my luggage. Put DND on my door & leave the TV on loudly.
It's funny you asked this because I was on vacation in Califrornia for 3 weeks so my crazy ass brought 1 antigona, 1 chanel jumo and 3 saint laurent bags. I locked them in my carry on luggage every time I went out. I try and keep the luggage out of sight and put some folded clothes on top of it..Not sure if that makes a difference. But be sure to get a lock for your luggage!