I purchased a vacation rental in the winter of 2019.

I would choose a place that doesn't have the frozen pipes/ice, snow damage and hassle risk, yet close to winter recreation. 

Here's my issue....My original offer stated that the utilities would be on and de-winterized prior to the inspection. 

It's both wishful thinking and even if fulfilled, the potential home value has to be sold to be realized.Now, that being said, I don't know when you started to look in the summer, but middle of winter is historically the bottom of inventory.

Easier/same/more difficult to rent in the winter? 

Interest rates will also rise within the next 6 to 12 months and we will start to see waves of foreclosures, evictions, and new home building (as building materials costs are stabilizing) driving up supply as we go into winter and spring 2022.

It's not like in the winter when there is a requirement for a certain amount of heat. 

I work in construction and occasionally am laid off during winter months and collect unemployment.

We had a nice discussion with them yesterday but towards the end they mentioned this issue, I do not yet have more information but I am going to talk to them again...Side bedroom of this house has a winter only water issue where the wood flooring in the room rotted out and had to be replaced with carpet.

Tons of summer stuff in Grand Lake and near Winter Park Ski Resort for Winter.Breckenridge is also generating a lot of events in the summertime, they used to be the start of the Pro-Am bike race I think.