Punting in the metropolis
I feel your pain
I have that situation sometimes in Europe. I've a wide selection of clothes (including a suit for times I need it) with zip pockets and inside pockets. I'm into this sort of stuff so if anybody wants more details and ideas they can pm me as I don't intend to put too much info on the open forum or to newbies with no reviews.
If you don't have clothes with zipped/concealed pockets, and don't want to buy them, you can get sew-on inside pockets. When you take your kegs off, roll trousers up, belt first so stuff doesn't fall out of pockets, place on top of shoes where you can see them from the top of the bed. Put shirt and socks on top neatly. If you plan to have a shower, get undressed in the bathroom and bring the rolled up trousers back with you. That way it's more natural. I never carry a wallet for such situations unless it's essential for something else. Folded money and cards can be concealed: a wallet less easily. For smaller amounts or credit cards, there's small armbands used by joggers that have a concealed zip.
For an overnighter, put your trousers, with valuables, under the mattress "to press them" or preferably when she's in the shower and lock your rucksack to a pipe or the bedstead with a small steel locking cable. Some people trust hotel safes. If you have lots of stuff, don't put all your cash and cards in the same pocket. If you have a laptop make sure your laptop bag or rucksack has a combination lock. Make sure your phone is switched completely off so it can't ring (easy to lose things if you suddenly jump up to get phone from pocket). Androids are less homogenous but modern iPads and iPhones are fairly bullet-proof as long as no-one can guess your password.
The thing is, get all your security routine solid and then it's easy to relax. Example, was shagging a hottie in a tiny dimly-lit developing country backstreet room. We're humping away and I notice her hand is trying to check the pockets of my trousers. I didn't freak as I was enjoying the fucking. Just laughed and tapped her arm and told there was nothing there (it was in my boots). Most of this is far more security than most people will need but just ease it to your comfort zone. If you do get robbed, try not to let it spoil your day, think of it as 'punting tax' or something and hopefully it wasn't for much. Get straight back in the saddle or it'll make you paranoid.
At the risk of sounding OTT to many, hope this helps anyone that might need it!