Hotel booking criteria

How old the property is isn’t of any relevance to me, as I have stayed in good and not so good older/newer properties. Older can mean thicker wall, thus better sound insulation.

I always ask how quiet the place is as I’m a light sleeper.

What is the parking provision?

Where is the property in relation to public transport?

Depending on when and where I am travelling - does it have heating/ AC?

I ensure that I have the full address so I can check it out on Google Maps Streetview.

Because bathrooms are so often squeezed into older properties, I always find out where the bathroom is. Twice we have found in apartments in Italy that the bathroom's up or down a VERY narrow flight of stairs that I wasn't expecting, despite looking at all the photos carefully. "Narrow" like you have to turn sideways kind of narrow. Not so good in the middle of the night.

This year, for a trip to Puglia with adult children and very young grandchildren, I was about to book a place when I found out that the second bathroom was outdoors in a separate building.

I often wish all airbnb and other rental properties would include with their photos even a rough sketch of where all the rooms are.

I agree to ask about the amount of stairs, both to get to the apartment and inside the apartment.
Many places have AC, but sometimes it is dependent on the time of year and there may be an extra charge, so I would confirm that.
Confirm how you will communicate with the host. 24/7 may not be necessary, but ensure you know how (email, text, etc.) and check your cell phone/data plans to be prepared for how you'll have to communicate.
Read all the reviews, sometimes there is specific information that may be useful.
Hope this helps. A month in Europe, what fun!

How do you ask about smells? Does your place stink? We've stayed in places that smelled musty/moldy and brought on breathing problems for those in our group with breathing problems. Old built up smoke smells don't go away with a spray of air freshener. Once we stayed in a cabin that smelled so terribly of moth balls that it woke me up in the night.

Not to get into the AirBnB discussion (really!) but I think if you are particularly sensitive to smells a hotel may be best. There is usually a general level of cleanliness, and they can more easily move you to a different room.

Thanks for the responses so far. I changed the title of the post in hopes of getting more responses.

I actively use the information, ratings, maps and customer reviews on Booking.com and Expedia.com, and have rarely if ever been let down. If there are many stairs, bad smells, a noisy bar downstairs, if the AC or wi-fi don't work well, if the breakfast is not good, if the bathrooms are tiny, then some people will mention those things, and they will be reflected in the ratings.

I use trip advisor, expedia and Booking a lot for reviews. They usually cover a lot of these 'downsides'

We are still quite young so stairs are not much of an issue and although very low maintenance otherwise, I refuse to share a bathroom so I always make sure to ask that my room have its own bathroom. I also ask about A/C and heat, sometimes amenities like laundry and as others, proximity to public transportation or parking if we are travelling by car.

Like Larry and Sharon, we use reviews on sites like TripAdvisor, booking.com, and hotels.com to screen hotels or B&B's. Usually the listings will have a pretty good run down of all of the amenities, a Google map, and the reviews are likely to mention deficiencies. But it sounds like the OPs concerns aren't so much with hotels as with Airbnbs. The uncertainty factor with these is one of the reasons we tend to stay in hotels.

Another person who leans on booking.com and TA for reviews and pictures of recent property condition.

Things I look for: spotlessly clean, remodeled or rehabbed in the past 10 or so years, quiet, wifi included, comfortable beds, parking situation/distance to mass transit depending on what we need for that part of the trip

Things I don't really care about: quality of breakfast (there's almost always a place down the street where we can grab coffee/tea and pastries) if the staff are 'friendly'- I'm fine with competent and a bit surly, stair or elevator situation if four floors or less

One of the things most lodging sites still have not quite got right is to specify whether a private bathroom is also 'immediately accessible from within the room'. A private external bathroom is surely much better than a shared bathroom but it surely bothers me a lot. Guesthouses are the most likely culprit of this.

Another pet peeve of mine, when traveling with companions other than a SO, are rooms that have transparent or semi-transparent showers, i.e., rooms where one directly sees the shower compartment/cabin/tub from the bed without any meaningful wall, division etc. That is a trend in several remodeled hotels. It works with a SO, but it creates awkward situations if you are traveling with someone else and cannot take a full shower with some reasonable privacy.