Op, sorry I hated using Disney bus transportation with a stroller especially during a crowded period.
Sorry posters but imo unless you are on a monorail line (which op won't be) when you have a child or children in strollers the buses are hell. I was much happier even when I stayed on site, simply getting in my car, no pushing, no trying to finagel (sp) the stroller because the buses were packed to the gills.
sorry, when you got crowds and strollers, disney transportation is any thing but easy. don't even get me started with the "park closing" mad rush to get to values bus experience.
Look at Buena Vista Suites only 2 miles from Wd .. Not bad but not like disney.. Look at All Star very reasonable..
You will get opinions on both sides of the fence on this one. I am an onsite person. Love it, have no desire to stay offsite. I know it can be cheaper. I don't like driving in a strange city, I don't like traffic. Both are things you will have to deal with. We also really like the dining plans which you cannot get if you stay offsite. Park hopping may be harder if you have to go get your vehicle and then drive to the other park versus hopping a boat or monorail over. Just some thoughts
.
On site!!! No driving or parking, love the extra magic hours and we also like to go to the room several times during the day.
I would also chime in by saying that if you are truly choosing to go over Christmas, and I mean Christmas Eve and Christmas Day, that if the parks get to capacity, off-site people will be the first ones to be refused admission. If you stay onsite you are at least guaranteed admission into a park for the day.
I would seriously consider going at a more quiet, less croweded and less expensive time for your first trip.

The rule of thumb for off-site guests is once the parking lot is closed in the morning so is the park. WDW resort guests can usually still get in via their resort buses and the monorail, but I have see CMs checking resort IDs at the bottom of the monorail ramp to Epcot in the early afternoon to limit access to the MK.I was going to say the same thing. There is NO WAY I would ever go to Disney on or just after Christmas day. It's packed and like what was said here, if you stay off site you may not even get in.
). Our sleeping arrangements will be as follows: my mother and father, along with my adult sister and my DS who will be 7 will share the bedroom. Mom/Dad/DS go to sleep early, so it makes sense for them to be in the room. DH and I will take the murphy bed in the living room (although I'll probably end up squishing on the couch....he's a bed hog
). The cabins are $450 per night over the 2011 holiday seasonAnother option that I haven't seen mentioned is the Cabins at Fort Wilderness. They're close to the MK and the monorail, but still should have space.
.