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Making it in Big Sky: Natural Retreats

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Tim Drain is the regional manager of business development at Natural Retreats in Big Sky. PHOTO COURTESY OF TIM DRAIN

By Mira Brody EBS STAFF

BIG SKY – While Big Sky as a full time community is growing, the area sees around a million visitors a year. Serving these visitors are businesses like Natural Retreats, who provide high-end luxury rental homes so those visiting can be at ease during their stay. Natural Retreats also provides transportation and touring outfitter services so they can gain the full Big Sky experience.

Explore Big Sky spoke with Natural Retreats’ Regional Manager of Business Development, Tim Drain. Drain says Natural Retreats’ focus is on quality service for renters and homeowners, and stresses that they are selective about the properties in their portfolio. Natural Retreats favors properties that would not be well-suited for long-term housing so as not to add to the housing market challenges for locals in Big Sky—a balance of brand standards and community needs.

This series is part of a paid partnership with the Big Sky Chamber of Commerce. The following answers have been edited for brevity.

Explore Big Sky: I’d like to start with a little background information on you, when did you come to Big Sky? 

Tim Drain: My wife Kristin and I moved here in the fall of 2010 from northwest Washington and have lived and worked in Big Sky ever since. Kristin had spent the ten years prior in the San Juan Islands where we met while I was splitting my seasons between Mt. Baker in the winters and the San Juans in the summers. We planned initially to spend the winter in Big Sky and return to the San Juans for the summer but then seasonal work led to year-round work for both of us and after spending the first summer of life and the first in many years of Kristin’s life away from the ocean, we were hooked and we never looked back.

EBS: Tell me about the history of Natural Retreats. When did it first open? What is your role there?

T.D.: Natural Retreats opened its doors in Big Sky late in 2015 with the acquisition of Vacation Big Sky. I was the General Manager from shortly after that time until the summer of 2021. At that time I moved into a new role as the Regional Manager of Business Development for the Big Sky market.

EBS: How has Natural Retreats grown over the years?

T.D.: Natural Retreats grown in many ways since 2015. We have grown locally in Big Sky both in terms of business levels and our team. Over the past six years we have grown and refined our portfolio to focus on the highest-end luxury homes here in Big Sky. We have proven with our team of local property managers and access to well-qualified luxury travelers that we are the experts in managing luxury vacation rental homes ranging from ski-in/ski-out condos to one-of-a-kind custom homes.

EBS: How big is your team?

T.D.: In the six years Natural Retreats has been operating in Big Sky we have doubled our local on-site team from five fulltime year-round employees including property managers, owner services, and guest service to a team of ten, increasing staffing levels in every area of our operations. We also partner with several long-time local vendors for specialized services and we consider these key partners an extension of our team. I am proud of not only the performance we have provided our homeowners, but more importantly the fact the we are able to offer more local Big Sky residents well-paying fulltime careers with industry leading benefits.

EBS: Tell me about the different services offered at Natural Retreats?

T.D.: Natural Retreats is a full-service luxury vacation rental management company. We provide a full scope of property management services and vacation rental representation to the homeowner partners in our portfolio. We take the stress out owning a vacation rental home by handling all of the maintenance, housekeeping, vendor relationships, bookings and guest service so our homeowners can focus on their lives back home while generating income and [enjoying] spending their vacations at their homes here in Big Sky.

“I am proud of not only the performance we have provided our homeowners, but more importantly the fact that we are able to offer more local Big Sky residents well-paying fulltime careers with industry leading benefits.”

Tim Drain, Regional Manager of Business Development, Natural Retreats

We also operate a transportation business and Yellowstone touring outfitter. Shuttle To Big Sky provides private and shared airport transfers between Bozeman Yellowstone International Airport and Big Sky as well as local transportation services ranging from shuttles between our visitors’ accommodations and their favorite restaurants to private event charters. Yellowstone Luxury tours provides private, custom day tours of Yellowstone National Park for visitors staying in Big Sky, Bozeman, West Yellowstone, and Paradise Valley.

EBS: What is the best part of working at Natural Retreats?

T.D.: There are a lot of benefits to working at Natural Retreats. One of my favorites is what we call “NR Days,” which is an additional five paid vacation days on top of our PTO plus a lodging stipend for any of our destinations across the county. On top of the benefits, we have a great team of passionate hospitality and property management professionals, all of which have their own love for the endless adventures Big Sky provides.

EBS: What is the best business advice you have ever received?

T.D.: It all comes down to work ethic and doing what you enjoy. Do what you love, work where you want to spend your time, and don’t take anything for granted. Success—for you and your customers—will follow in due time if you put in an honest day’s work every day and feel good about putting your signature on your work.

EBS: Anything else you would like to add that the Big Sky community should know?

T.D.: I consider myself very lucky to not only live in one of the most special places on earth, but also to be a part of the evolution of Big Sky both as a destination and as a community. I’m proud that Natural Retreats invests in the communities where we operate, from providing well-paying careers to supporting local community events and initiatives.

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