Hotels are one thing that can make or break your vacation. Unless money is no concern, the challenge is to find the best hotel, in the best location that your budget will allow.
This is one area on which I’m willing to splurge because your hotel can/should be your sanctuary when traveling, particularly if something is less than perfect about your trip (i.e., travel delays, bad weather, long lines at sites, illness, tired feet, etc.). This is also true when booking your rooms from individuals using sites such as Airbnb, and VRBO (Vacation Rentals by Owner).
If I don’t want to stay in a large chain hotel (i.e., Marriott, Hyatt, etc.) I typically look for interesting boutique hotels or I book a room or studio in a personal residence (or the entire house) in areas I hope will allow me to experience what it’s like to actually live in a particular city.
RULE #1: Once you know where you want to stay, always book directly with the hotel to avoid possible problems going thru a 3rd party intermediary. The primary reason is that if you’ve booked directly with the hotel and something goes wrong, then you only need to deal with the hotel to try to straighten things out. On the other hand, for example, if you booked a room thru TripAdvisor, and if something goes wrong, you may wind up in a situation where the hotel tells you to talk to TripAdvisor, and vice versa. Not a fun place to be when you’re standing in the lobby of a hotel in a foreign city that doesn’t have a room for you that you thought you booked.
Another reason to book directly with the hotel is that their prices are typically identical to those you can find on 3rd party sites. And even if you can find a room for a cheaper price, there's usually a reason why the price is less (such as the room being located directly above the garbage cans… that get picked up every morning at 5:00).
Boutique Hotels: When looking for boutique hotels, I typically use TripAdvisor to research places to stay. I rely primarily on customer reviews/ratings to determine where I want to stay and have never gone wrong (knock on wood). There are often numerous customer photos to help you get a good feel for the place (vs. professionally taken, hotel approved photos). I usually book a top 10 rated hotel, and give greater weight to hotels with the most number of reviews.
Breakfast Tip: If given the choice, always take (and pay for) the option to have breakfast included in your room price. It’s a lot nicer to roll out of bed, into the shower and then downstairs to get your first meal of the day, versus having to go out and look for a place to eat. Outside restaurants, cafes, etc. are great for lunch and dinner, but I usually don’t want to think that much early in the morning.
Airbnb, VRBO, etc.: I’ve used both of these sites for booking a room, suite or house and have never had a bad experience. Like booking a hotel, customer reviews and photos play a big part in my decision making process, and I am only willing to consider a place that has a lot of customer reviews.
The only other consideration for booking part or all of a private residence is location. Since you won’t have the amenities you normally get with a hotel (e.g., an in-house restaurant where you can get breakfast) it’s best to be located close to the center of town so you can easily pick up the groceries you want/need for your stay.