I had booked one nite here for feb 3rd 2012, at time of booking I specifically asked if bad weather prevented me from getting to Winterpark would I be allowed to cancel with no charge, the gal said sure no problem. Lo and behold heavy snow with over 600 flight cancellations into Denver occured on that day. My flight was not cancelled, I made the wise decision to cancel on my own. CDOT had highway closings and a warning to stay off the roads and I was not about to get stranded in a rental car in the mountains. Called and talked to Kristin, she refused to refund me and charged my credit card the full amount. Bottom line, they could care less about anyones safety and I doubt if they care about your experience if you do make it there. STAY AWAY, FAR AWAY. Mike in St. Louis.

... it may make a difference who you book through. We booked with priceline, who referred us (via a company called leisurelink) to alpine resort properties. That created some hassle:
-upon arrival (at 7:30pm, after our flight and 90 min drive from Denver, with 2 hungry and tired kids), the front desk told us told us that the management company we booked through is separate from the resort and that we have to check in - in person - with the above management company in the town of Winter park (the front desk first called for us and thought they would just phone in the code but they required us to drive the few miles to their office - I wonder what they would have done if we arrived by shuttle). That driving and the delay wasn't really necessary, only to get a 6 digit door code and a photocopied map that they had at the front desk as well. I also reread the check in procedure Email from leisurelink and it is really not at all clear whether the check in during winter is "on site" (or in the town of Winter Park as it is during summer).
-we asked this management company for a late (noon) checkout and they were so kind to do that ... but forgot to give us new codes as the locks apparently change code exactly at the preprogrammed check out time (which was 10 am, just came to the resort from the slopes at 10:05 am and was lucky to get into the building without walking 1/2 a mile to the main entrance because someone just happened to leave). Another call to alpine was needed in order to receive a new code. In any case, for any request, be it towels, blanket etc., the front desk will refer you to alpine if your booking connects you to them. They (alpine) seemed OK except for the above hassles already mentioned (and they have a 24 hour service) but it's obviously not the same thing as having someone at the resort front desk ready to help you.

The resort/condo hotel itself is well maintained and has nice facilities (nice indoor/outdoorpool, fitness center), the condo was not large but reasonable in size, well equipped and nicely renovated. As others pointed out, Ski in is for intermediate or better skiers only (ski out is an easy green catwalk). Would come here again any time (but probably try to avoid alpine).

We stayed five days in a one-bedroom unit on one of the upper floors and enjoyed the convenient ski-in / ski-out. This room was nicely decorated and had a full kitchen. It seemed to be individually owned and rented out as part of the Iron Horse Resort, so I assume each unit might be different and therefore it's not possible to give a general rating for other units.
The pool area is nothing special, but the waiter from the nearby restaurant serves this area and brings the beverages right to the hot tube. Small gym only and no sauna, which would be nice during the winter time.
Despite the advantage of the slop side location, there is nothing close by other than the one restaurant of the property. However, a 10 minute walk along the ski track leads to the Winter Park Resort with shops, bars and entertainment. A free shuttle bus brings you to Downtown Winter Park with all required services, and runs until midnight during the season.

This was our first trip to Winter Park. There may be better options that the regulars know of, but based on our experience we liked the Iron Horse. Is it a luxury resort? No. Is it easy ski in-ski out for all levels? No. But for a last-minute get away to do some early season skiing with two snowboard-novice kids, it was perfect, and a great value.
Overall/room: We stayed 2 nights early the week of Thanksgiving in a 1-bed/1-bath and the price included 2 adult lift tickets. If you deduct the cost of the lift tickets, we spent about $70/per night. It was one of rooms owned by the resort, as opposed to a 3rd party owner. No issues at check in with the room, but we did have to go to the village to get our lift tickets. They have an on-site ski rental shop but we ended up just getting everything in the village. Be warned you can't walk to the village or the parking area (that has a gondola to the village). It is a 2 min drive to the parking lot, or they have shuttles. This wasn't a big deal for us as being early season the hotel and mountain wasn't packed. Might be an issue during the weekends later in the season. The room we were assigned had a small bedroom with one large bed, a full size Murphy bed, and a sofa sleeper. Worked great for us taking 2 kids along, as they both had their own bed. The main bed was comfortable, though the pillows were way too large. Plenty of blankets though for the three beds, and a nice gas fireplace for heat and ambiance. The room also had a kitchen with fridge, oven, microwave, dishwasher, so very convenient for making dinner the night after we skied. We were also given a spot in the parking garage, so that was nice. Not sure how that would work when its busy though--the garage is tiny. There was a flatscreen TV in the main room, and a small one in the bedroom that wasn't hooked into cable. So plan on watching in the main room.
Amenities: Dinner at the onsite Bistro the first night was great. Food and service were exemplary, and the prices were not bad for a ski town. Nice, smallish indoor/outdoor pool the kids loved. And two large hot tubs as well (only one was open). Also has a nice work-out facility if you didn't get enough on the slopes. Our room was really far away from these, and to stay indoors you had to go up and around to access the skyway. Not the worst thing in the world, but made for a chilly walk back after the hot tub.
Etc.: Only real issue with the room was that it was next to the washer/dryer room, and someone was using it til about 10 at night. After a long day of skiing that noise next to the bedroom wasn't appreciated. So if you can, request a room away from that (we didn't know until we go to the room). I'd worry a bit that the thin walls would mean lots of noise if the hotel was fuller--there were not many people at the resort this time of year. I'd would imagine that the place could be a little cramped on weekends if they are full (the parking garage, small pool, small restaurant...)
Verdict: If you can get it for the right price and you don't mind not being right on the mountain this is good option in Winter Park, especially in the non-peak times when you are more likely to have the amenities to yourself.