This feature originally appeared in the October issue of TransWorld SNOWboarding. Subscribe here.

Words: Tyler Macleod

In August of 2011, I made the spontaneous decision to move from my hometown outside Baltimore, Maryland, to Winter Park, Colorado. It was a small resort town I had no prior knowledge of, making the choice to move there all the more odd to my parents, family, and friends. I had graduated college three months prior and was fortunate to lock down a reputable internship, transitioning into a lucrative, full-time gig, so its easy to imagine the degree to which eyebrows were raised. Still, the depression that came with ironing a collared shirt every morning for my ensuing ten hours behind a desk was eating at my soul. I could see my passion for snowboarding fading in the rear view mirror during my hour-long commute each morning, just as it already had for many of my old on-hill companions. It was the recipe for a spur-of-the-moment, life-altering decision at the ripe old age of 23. A quarter-life crisis some might call it.

I didnt know a soul in Winter Park, but its down-to-earth atmosphere made for an easy transition. After a short period of time, I locked down a two-bedroom apartment with my girlfriend for a mere $575 a month. There was no waitlist, no bidding war, no struggle. I put in an application, and within a few days we were moving in. I was living the local lifestyle without a care in the world, paying my bills with an $11 an hour wage from tuning skis, and of course, snowboarding every single day.

For mountain communities, lack of housing has translated to workforce scarcity. The days of tuning boards to pay the rent are getting tougher. | PHOTO: Andrew Miller

In 2018, that same unit is going for three times as much, and youll have to take a number and wait in line for a chance at it. A portion of the apartments in the complex have even been scooped up by Winter Park Resort to be used as their own employee housing. As is the case in many other mountain towns across North America, the amount of housing wanted ads now far exceeds the amount of for rent listings. When I moved here, there were plenty of rental options but a scarcity of jobs. In 2018, every business has a help wanted sign on its door.

But for those who come to vacation throughout the year, finding a place to stay couldnt be more painless. With the dawn of Airbnb and similar platforms, finding a home away from home is easier than ever. It just means a local may no longer have a place to live.

Instead, they might be living out of their car, with multiple jobs, questioning whether the choice to leave a desk job was the right decision after all. Theyre lucky if they find time to snowboard, and the quarter-life crisis has resurfaced.

Like them, Ive resorted to picking up additional work to make ends meet. Ironically, my second job is cleaning short-term rental units. And business is booming. As often as I walk into these units thinking a local could be living here, its hard not to consider the owners position as well. Theres money to be made, and its easier to point the finger when youre not in their shoes.

Is the Blame on Airbnb Warranted?

If youve lived in a mountain townor any destination area for that matteryoure familiar with the kneejerk reactions of crusty locals. Its always easy to place the blame on everything from tourists to corporate resort entities for any issue that arises in the community, and while sometimes warranted, other times these are excuses for lack of effort. Which led me to consider whether Airbnb, VRBO, and similar short-term rental services in general, are to blame for the lack of housing options, let alone affordable ones. Are these platforms actually destroying the very essence of my own mountain community of Winter Park, alongside most other major ski towns?

Robin Van Gyn, who rents her Whistler home out via Airbnb when shes traveling, seems to agree. But she also realizes that, like all issues, there are two sides.

It does contribute to the problem, she says. There is no housing for the workforce, and people cant afford to live. Its insane.

But its also another source of income, so [as a homeowner] its hard not to, she admits. Were all just trying to get ahead.

Robin Van Gyn, who rents out her Whistler home via Airbnb, realizes there are two sides to the short-term rental issue. | PHOTO: Robin Van Gyn

Its a sentiment thats echoed by Winter Park local turned part-time Tahoe resident Jackson Fowler, who, like Van Gyn, has a property hes rented out via Airbnb for the past three years.

Ive seen both sides of it, being a snowboard bum and having experienced the struggle to rent a room in Tahoe where a similar crisis is going on, Fowler explains. Everybody is turning to the Airbnb thing. That kind of leaves the locals in the dust, and I feel for that for sure. But, at the same time, the money I make from renting my house helps me get by.

While its easy to blame homeowners who opt to rent a unit out short-term rather than long-term, assuming its a decision based solely on profit potential, for some, the latter is hardly an option. Van Gyn and Fowler both spend time each winter traveling to snowboard but still need a home base to come back to. Why not make a few bucks rather than leave it vacant?

While traveling for turns like this, Robin Van Gyn has rented her unit on Airbnb to turn its otherwise vacant days into extra income. | PHOTO: Tim Zimmerman

I might as well do something with it, Fowler says. And then I still have it open when I need it. I can always just block off dates on Airbnb, but I cant kick out a full-time renter. I cant just say Hey, Im coming up. Can you leave?

But that consistent inconsistency is something Van Gyn admits to struggling with.

Its hard to move your personal things all the time, she says. Sometimes you just want your space to be there and not have to screw with it. Its work.

As enticing as the extra income can be, its not always worth it.

Short-term is a pain in the butt, she readily admits. Long-term is the way to go if you can make it work.

The Rise of Short-Term Rentals

With short-term rentals rising in popularity for both homeowners and vacationers, there had to be some quantifiable proof out there. Are STRs, as theyre acronymized, actually taking long-term opportunities off the market, or are they simply filling otherwise vacant properties?

In my search for answers, I immediately took to the first source that came to mind: the ever-reputable Craigslist. At the least, I wanted to know how many long-term housing options were available, beginning in my own community of Winter Park.

How many did I find? Just four. The cheapest was a dated, single-bedroom unit for $1,400 a month with no utilities included. A two-bedroom was also available up the road in neighboring Fraser for $1,500, which included a disclaimer stating that long-term lease agreements would increase, at an undisclosed amount, during ski season. I also found a two-bedroom unit in downtown Winter Park for $3,000 per month. The fourth was presumably a scam, as it was listed multiple times for $950 and wouldnt be available for another two months anyhow.

What about the local newspaper listings? Surely there had to be something listed there.

Nope. Absolutely nothing.

After talking to Fowler, who is actually switching his Airbnb unit back to a long-term rental because of a recent knee injury, that shortage became even more apparent.

Its been insane since Ive put the house up as a full-time rental, he said. Ive gotten 50-plus phone calls in the past two days, and a ton of emails. I listed it at $1,600 for a two-bedroom, not including utilities, which, for Winter Park, is actually pretty low right now.

From renting out his home in Winter Park, Colorado, to living out of his truck, Jackson Fowler knows a thing or two about the mountain town housing landscape. | PHOTO Danny Kern

Perhaps the pool of Winter Park rentals is relatively small to begin withmaybe the lack of available housing is due to a lack of housing, period. Not the case. l conducted a search of the Winter Park area on Airbnb, which resulted in a surplus of 300 short-term rentals.

I performed a similar search in a number of other mountain communities, from the nearby Colorado ski mecca of Breckenridge to the housing crisis capital that is Jackson, Wyoming. The results, unsurprisingly, werent much different. While long-term listings in local papers and online were both expensive and hard to come by, Airbnb was overflowing with potential short-term rental opportunities.

Still, when it comes to workforce housing shortages, not everyone is ready to point the finger at STRs.

A lot of blame is placed on short-term rentals, admits Town of Winter Park Housing Manager, John Crone. But Im not really sure there is that much blame that can go there. It has certainly taken some long-term rentals off the market, but I think most of those short-term rentals are the types that sit empty most of the time anyways.

As more homeowners favor Airbnb, locals will continue to struggle to make the Whistler backcountry their personal backyard. Jody Wachniak takes advantage of some prime real estate. | PHOTO: Andy Wright

According to, which provides a market overview on rentals for a submitted zip code, these STRs arent always proving to be as lucrative as one might expectat least not in Winter Park. Despite an average daily rate of $209, STRs in Winter Park are only yielding a 16% occupancy rate, which results in an average monthly revenue of only $1,003. That revenue doesnt include taxes or service fees that the town charges either, ultimately providing an average monthly revenue that sits well below the current $1,400-$2,000 monthly range I saw for long-term two-bedroom units.  

Revenue aside, Winter Park has witnessed incredible growth in the quantity of STRs available. After starting with only six total cumulative rentals in 2011, that amount has now increased to a whopping 2,410 in 2018, according to Whether these rentals were sitting vacant before Airbnb or not, they arent sitting vacant anymore, and the rate at which theyre increasing is significant.

And what does AirDNA say for Breckenridge and Jackson? Breckenridge has more than twice the occupancy rate of Winter Park at 33%, while Jackson has an even higher rate of 60%. Breckenridge yields an average monthly revenue of $2,627 and has increased from 12 total rentals in 2011 to 6,744 in 2018. Jackson, with an average monthly revenue of an impressive $6,254, showed an increase from only one unit in 2010 to its current 545 total units.

Looking at the South Lake Tahoe area, the results are similar to that of Breckenridge. AirDNA shows an average monthly revenue of $3,604 by way of a 43% occupancy rate. Since 2010, the total cumulative rentals here have increased from just 15 to a whopping 4,610.

In Tahoe, Fowler has seen these effects firsthand.

I had a group of friends in a four or five bedroom house. Their lease was up, and they were planning to renew, but the homeowners decided to switch to the Airbnb thing. They were left in the dust, thinking they had a house for another year.

While the magnitude of these numbers undoubtedly requires context of each towns population to appropriately put into perspectiveWinter Park has a population of just over 1,000, while South Lake Tahoe exceeds 20,000the fact of the matter is that the number of STRs is rising, and rising dramatically. Surely, it has some sort of effect on the existing workforce housing shortages.

Is There an Effect on the Workforce Housing Shortage?

In Summit County, Colorado, home to the aforementioned town of Breckenridge, thats what officials are bent on finding out.

In general, we get a sense that they are having a large impact, says Jason Dietz, executive director for the Summit Combined Housing Authority. One of the things we want to try to do is quantify what that is [through] working with the towns that make up the Summit Combined Housing Authority. We dont really have a quantifiable number that we can point to with hard data right now.

Currently, Summit County, which is comprised of various communities including the towns of Breckenridge, Frisco, Silverthorne, and Dillon, while also encompassing popular ski destinations such as Copper, Keystone, Arapahoe Basin, and of course, the resort Breckenridge, is in the process of putting together a study for a new housing needs assessment that hopes to zero in on exactly how STRs are impacting local housing across the county.

We want to understand, Are we making any headway in getting more workforce housing, or are we staying the same, or going backwards? explains Dietz. While Summit County has long been ahead of the curve in developing workforce housing projectsthey have a surplus of 500 units across the county currently in the works to be developedthere is concern as to whether the projects are keeping up with the simultaneous growth in STRs.

We dont really know the answer to that, admits Dietz. Were looking to try forming an RFP (request for proposal) that will quantify that to see what the real numbers are.

To make the situation more difficult, Summit Countys five jurisdictions each regulate their own communities when it comes to STRs. While Breckenridge has been regulating STRs for some time now, which includes remitting a 3.4% tax on short-term lodging back to the town, the area defined as Summit County Unincorporated currently has no regulations.

There is zero regulation, says Dietz. Literally none in regards to it. But that is soon to end because they have been working on putting together regulation since last year, and they are in the process of finalizing that. The goal is to have some in place before winter.

Planned developments in Summit County, Colorado aim to ease increasing difficulty in finding a place down the street from the region’s world-class parks. Brett Moody enjoying bluebird park laps at Keystone’s popular A51 park. | PHOTO: Chip Proulx

For communities like Jackson, Wyoming, where STRs are just another hurdle on a long path toward workforce housing solutions, regulations are essential. And strict.

They certainly have [affected the housing shortage], says April Norton, Director of the Jackson/Teton County Affordable Housing Department when asked whether STRs have had an impact on the communitys current housing dilemma. Theyve taken housing stock out of the rental market. Theyve also inflated the values of the land here.

But according to Norton, STRs are just additional fuel to an already burning fire.

In Teton County, 97% of the land is publicly owned. Were already working with such a finite amount of land, that yes, the short-term rentals have certainly helped to inflate the prices, she says. But the bottom line is our land values are in no way tied to local wages either, so youre just fundamentally going to have issues with housing local workers.

This explains tough regulations on STRsincluding a lodging overlay and a minimum rental period of 31 days.

Pursuant to the Land Development Regulations Section 6.1.4.A Residential Uses, no private or residential unit may be rented for less than 31 days unless its included on an approved list of short-term rental units. While this should make it more difficult for STRs to have a substantial impression on the existing housing shortage, Norton admits that not everyone is a law-abiding citizen.

What theyll do is write a lease for 31 days, but theyll only rent it for a weekend, she says. So people who are trying to legally do it will do just that; they will rent to one person per 31 days. But a lot of other people will just blatantly disregard the rules, and if they get caught, they will be fined. But if they dont get caught, then theyre rolling in money because its certainly a lucrative thing to do.

In Whistler, its not uncommon for Airbnb owners to be less than honest in their handling of business either.

You have to be zoned for nightly rentals to rent [short-term], Van Gyn points out. I bought my place knowing that, but a lot of people do it illegally which is a bit shitty for properties like mine.

Whistler – like Jackson, Summit County, and so many other mountain towns – is no stranger to workforce housing woes, and short-term rentals don’t appear to be helping. | PHOTO: Scott Serfas

Effect on the Community

As mountain town work to regulate the impact of short-term rentals, or strive to find out whether they have a quantifiable impact, those who live and work in these communities deal with not only the potential that STRs are stripping them from potential housing opportunities, affordable or not, but also the impact they have on the character and atmosphere of a place they work hard to call home.

Karen Fisher, who lived in Jackson, Wyoming, from December 2009 to May 2016, experienced this firsthand.

When I lived in Jackson, I lived in the Village for a little while. Almost every apartment in our complexa 16-plex I thinkwas a short-term rental spot, she reflects. And the two buildings next to us, the same sort of deal. Everyone knew their actual neighborsthe people who lived therebecause there were only maybe six permanent residents in what? 48 apartments? The rest were all rentals and Airbnbs. Our next door neighbors were these Texans who came once a year but rented the unit all year long.

At one point, with the workforce housing market as bad as it was, Fisher had no other choice than to live in a garage. For Fisher, it was more than acceptable compared to other options, or lack thereof, the city had available.

The garage wasnt bad, she admits. It had running water, a washer, dryer, sink, wood burning stove, and even a bathtub. It wasnt very energy efficient though. Cold as hell in there.

For Fisher, STRs meant trading a once supportive community for a revolving door of vacation-minded visitors. While it can be argued that mountain towns only exist because of the tourists they host, in a place like Jackson, where the majority of the workforce makes 80% less than the median income, that idea becomes a hard pill to swallow.

A sense of community didnt exist for me in the Village, she says. Theres something to be said about having neighbors to help each other out, which we didnt really have.

And that lost sense of community was magnified depending on the season.

During summer, it was much busier because the renters were on their way to Yellowstone, she adds. So typically they were older and respectful, at least. The winters had fewer renters, but most were man-cation lets party a bunch and make loud noises types. That was tough while working early morning shifts. I wore earplugs.

Due to the increasingly impossible task of finding housing and slipping sense of community, Fisher left Jackson in the spring of 2016.

The only people I know that still live there are folks who bought houses more than ten years ago. Things dont add up. Its almost mandatory you have a trust or other source of income to live there, or just own a condo and have it as a rental and come out periodically on vacation.

Where once was “For Rent” signs, now are “Help Wanted” signs in their place. | PHOTO: Tyler Macleod

Where Do We Go From Here?

When I travel to snowboard, the inevitable question of where to stay arises. Would I choose to book a room at a hotel or, often for less money, avoid  interaction with a front desk agent and enjoy the comforts of home while I was away?

As easy as it is to harness a crusty local attitude and point the fingers at short-term rentals, one thing is certain: they arent going anywhere. And for those of us in the snowboard community, wed be lying if we didnt acknowledge the benefits they can providewhether its earning some extra income while out filming, or having a comfortable and affordable place to stay during the course of our winter travels.

But even without directly quantifying the impact short-term rentals are having on long-term mountain town housing, its safe to say they arent helping. Housing shortages are increasing at exponential rates, and unless communities and individuals take initiatives to find solutions, the effects will be dramatic.

In my home of Winter Park, the town has already constructed a 38-unit workforce housing complexone of those units fortunately belonging to myself. Theyve also broken ground on a 27-unit, 104-bedroom complex through a long-term lease with Winter Park Resort. This new relationship between the resort and the town will prove vital in providing adequate housing for local employees, both at the resort and throughout the rest of the community.

In nearby Summit County, numerous projects are either completed or underway, according to Dietz. The town of Silverthorne has broken ground on 200 workforce housing units, with 60 of them set to be available before this upcoming winter. Neighboring Keystone has 66 single family homes in the works, and Breckenridge, in addition to having recently wrapped up a project that provided 52 townhomes and 30 apartments, will also have another 18 units becoming available in the coming months.

The Town of Winter Park has taken strides in addressing the growing shortage of workforce housing options with a number of projects currently underway. | PHOTO: Tyler Macleod

Jackson is even making significant strides. According to Norton, the community approved a comprehensive plan in 2012 with the goal to house 65% of the workforce in town. Currently, they are at 59% and trending in the right direction. In addition to 28 units recently available in August, another 90 are expected to open up within the next year and a half. Jackson is also in the process of constructing 125 additional rental units, and while not all of them will be restricted, they will hopefully assist in driving rent down.

On an individual level, it could mean picking up another job for the time beingmaybe even cleaning some short-term rentals on the sideor finding a less-than-preferable place to call home for a bit. It might not be as cheap and easy as it once was to live in these places, but If youre committed to snowboarding, youll find a way to make it a reality.

All the people I know will make it work somehow or another, says Fowler. If they really want to snowboard, theyll either live in their car or stay on peoples couches. Airbnb is definitely making it harder to live in these places, but no matter what, Ive realized were all going to make it work one way or another.

And no matter how frustrating the housing climate becomes, I  promise you that ironing wax will always beat ironing a shirt.  


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