Now I will say that I do adjust my prices down for the winter to attract folks but I don't get many.

I had one were my PM calls me its in INDY cold winter they just had baby cant  afford the rent and heat just take no payment for 2 months then they will add the balance any pay it off.. well of course after 2 months they just left  LOL..

However, understanding all the costs of buying a real estate investment property will help you avoid costly mistakes.Buying a rental property, holiday home, or property to flip can yield short-term and long-term financial gains.

Also to eventually own a home within 50 miles of the Aspen CO area (winter/employment location). 

Based on the supply of homes for sale and the time of year, I predict home values will drop a little bit over this winter until early spring.

Our summers are WAY  busier than our winters.

So with all that, I'm thinking to open booking now for next summer with a 7 day minimum, see how it books out, and by late winter/spring I can reduce it to a 3 day min to fill any remaining weekends, and then work on filling mid-week vacancies as summer approaches.We were leaning towards Fri-Fri, but Michael I like your suggestion about the Mon-Mon option, which could be nice because renters would have the weekend to travel and then begin their stay on a Monday, then they would end their stay on an upnote with a long weekend...But with either Fri-Fri or Mon-Mon renters would probably need to take 6 days off work...Sunday-Sunday might actually be better because renters would only need 5 days off.  

I enjoy them.When I buy my 1.1k ish sqft for $200/ft and less than $275/mo HOA winter condo, I'll bring my own car and skates👍

I get a bit antsy considering the upcoming holidays and what demand looks like.

Something to be aware of.We've filled vacancies at our medium-term rental in Denver in January before, but had trouble in November and December, so I don't know if the winter is tough or if its simply the holiday season.I'd be more interested in buying the right place whenever it comes up.