We've done both and, if the cost is virtually the same, it's a tough call. Our offsite stays have been in condos at Windsor Hills and our onsite have varied - we've done All Star Music and Movies, CBR, and WL. Some things to consider:
At Windsor Hills
-- The drive to and from the park was not bad at all. We've done it in mid-Oct and late June - very quick and easy both times.
-- We rented 2 different condos from the same company and the people we dealt with were great. But, while both condos were nicely decorated and the furniture was pretty comfy, they were not outfitted equally in terms of towels, dishes, hangers, etc. That may sound like a small issue but it turned out to be a major pain - we were constantly having to do laundry and dishes so we'd be ready for the next meal or bath time. There were days that we had to adjust our park touring to accommodate doing the laundry. So little details like that can impact your experience more than you might think.
-- If you stay in a house or condo, you'll most likely have to do some housework before you leave. We've always been required to at least wash all the towels and dishes, strip the beds and leave the sheets in the washer, clean out the fridge and take out all trash. That may not sound like much but keep in mind that this is in addition to repacking all your stuff and loading it into your car. Depends on how much junk you take (I'm a heavy packer) but it can be quite a bit of work.
-- One of the reasons we chose the condo for our last trip was to save money by making full use of the kitchen. While it was nice having some homecooked meals, we ended up spending more time at the condo than I would have liked and less time making use of those very expensive park passes. I also spent more time than I cared to doing grocery shopping and, as mentioned above, doing dishes and cleaning the kitchen. So if I do offsite again, I'd probably just use the kitchen for quick meals we could grab and take with us (sandwiches and such) and as a place to store and warm up leftovers from restaurants.
If you stay onsite
-- Since you said you're driving, you'll have the option of using Disney transportation or driving yourselves to the park. Onsite guests don't have to pay for parking at the parks and you'd still have the option of splitting up if needed. Just make sure someone remembers to drive the car back to your resort.
-- No.Housework.At.All. 'Nuff said. (Can you tell I didn't care for doing housework on my "vacation"?)
-- Most resorts have plenty of food options right there just steps from your room. We LOVE the foodcourts. In my family, everybody always wants something different. We never seem to all want the same kind of food at the same time. With a foodcourt right there, this is no problem. Everybody can pick what they want.
It really is a very personal decision - there are so many variables to consider. But I hope this helped some.
At Windsor Hills
-- The drive to and from the park was not bad at all. We've done it in mid-Oct and late June - very quick and easy both times.
-- We rented 2 different condos from the same company and the people we dealt with were great. But, while both condos were nicely decorated and the furniture was pretty comfy, they were not outfitted equally in terms of towels, dishes, hangers, etc. That may sound like a small issue but it turned out to be a major pain - we were constantly having to do laundry and dishes so we'd be ready for the next meal or bath time. There were days that we had to adjust our park touring to accommodate doing the laundry. So little details like that can impact your experience more than you might think.
-- If you stay in a house or condo, you'll most likely have to do some housework before you leave. We've always been required to at least wash all the towels and dishes, strip the beds and leave the sheets in the washer, clean out the fridge and take out all trash. That may not sound like much but keep in mind that this is in addition to repacking all your stuff and loading it into your car. Depends on how much junk you take (I'm a heavy packer) but it can be quite a bit of work.
-- One of the reasons we chose the condo for our last trip was to save money by making full use of the kitchen. While it was nice having some homecooked meals, we ended up spending more time at the condo than I would have liked and less time making use of those very expensive park passes. I also spent more time than I cared to doing grocery shopping and, as mentioned above, doing dishes and cleaning the kitchen. So if I do offsite again, I'd probably just use the kitchen for quick meals we could grab and take with us (sandwiches and such) and as a place to store and warm up leftovers from restaurants.
If you stay onsite
-- Since you said you're driving, you'll have the option of using Disney transportation or driving yourselves to the park. Onsite guests don't have to pay for parking at the parks and you'd still have the option of splitting up if needed. Just make sure someone remembers to drive the car back to your resort.

-- No.Housework.At.All. 'Nuff said. (Can you tell I didn't care for doing housework on my "vacation"?)
-- Most resorts have plenty of food options right there just steps from your room. We LOVE the foodcourts. In my family, everybody always wants something different. We never seem to all want the same kind of food at the same time. With a foodcourt right there, this is no problem. Everybody can pick what they want.
It really is a very personal decision - there are so many variables to consider. But I hope this helped some.



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