The first thing you want to do when checking out holiday rentals is to narrow down the places where you want to vacation.
You should take into consideration the weather at the time of your holiday. Once you have that narrowed down you can begin your search. One might want to also consider price at the time of the holiday. It may be cheaper to go to cold climates in the fall and winter and warmer climates in the spring and summer.
Researching holiday rentals is much easier when you have the location picked out. There are a number of websites that cater to rentals during the holidays. You can always make it more personal and do the research yourself but that could be a lot of energy spent on a task that a computer could do for you. The advantage of using a computer is the realtime updates of pertinent information like price and availability. You may also want to consider amenities and events when booking your holiday rental. Decide what is important to you and try not to settle if you don't have to. Online searches can make this very easy for you to do.
Also consider the possibility of networking with people you know to create your own holiday rentals. You can swap homes or vacation homes with people you know or don't know, if by referral. This may be the option of choice if you are short on cash and really want the experience of going somewhere for the holidays. There is no one better to tell you about the happenings in a town than the people who live there. However, you should be sure to have a written agreement when choosing this option as it could get sticky if one party decides to pull out of the arrangement.