Guest post by Tyler Gillespie

I have worked directly with many hotels over the years and, as a result, I have a unique perspective on the different items and services that are offered to clients in the exclusive, high-end marketplace that is Aspen, Colorado.

In my opinion, in order to have a truly successful vacation rental business now and in the future, vacation rental owners should focus primarily on two things:

  1. The Customer Experience
  2. Treating Your Property Like a Business

Pay close attention! These are two areas hotels excel in, and you always want to make sure your property stays competitive.

Be more like a hotel…?

All over the Internet, experts in the vacation rental niche say: “Your vacation home needs to be more like a hotel.” But what does this mean, exactly? More importantly, how do you do that?

In The Hotelization of Vacation Rentals, a recent post on my blog, I provided a general outline of this concept. Now, I want to dive even deeper and explain why you (the homeowner) need to make sure the process and services related to your rental property are, well, “hotelesque.”

Two chairs and a sofa in a coworking space
Photo by Dan Gold / Unsplash

Services that surprise and delight, like apple pie

Let’s start with hotels. What is it about hotels that people love so much? One could say it’s because of their red carpet service, convenience, amenities, quality, and customer experience. Within the past few years, hotels have really stepped up their game!

(Interestingly enough, one of the reasons for this is because of increased pressure from the ever-growing vacation rental industry!)

For me, this topic brings to mind a recent story about an employee from the Little Nell Hotel, here in Aspen, who went above and beyond the call of duty to take care of his guests.

After a certain family visited, the employee took note of the their favorite dessert (apple pie!), added it to their file, and set a reminder on his own personal calendar to remember the exact date of a member of that family’s birthday. On this special day, he shipped them an Aspen apple pie with a personalized, hand-written note.

When they came back to visit, he always made sure an apple pie was ready upon their arrival. The end result? I’m willing to bet that this guest will be a Little Nell guest for many years to come.

What are you doing for your guests? Are you listening to their wishes, and going above and beyond? If you aren’t, you should be.

The old advice is true: Go above and beyond

Though a little extreme, I also love a story told in a recent article that was featured on, where – as a joke, he later revealed – a guest made some very strange requests when booking a hotel room.

Despite the weirdness, hotel staff responded like champs and, without hesitation, took care of everything asked of them.

a handful of M&Ms | "83/365" by Amy Loves Yah on flickr. (CC BY 2.0)

Here is an excerpt from the article:* “Three red M&Ms on the counter,” Wray, 28, said. “Not packages, just three single M&Ms. One for me, one for my girlfriend and one to split if we get hungry late at night,” Wray added in his request. Wray was traveling with his girlfriend, Lauren Taylor, from New Braunsels, Texas, and that wasn’t the end of the unusual request. ”And a picture of bacon on the bed,” Wray added. “I love pictures of bacon.”*

Now, am I saying that you have to do this for every guest?
Well, in essence, YES.

Going above and beyond—like this particular hotel did—is what it takes to stand out, be successful, encourage referrals and completely “wow” your guests.

Unfortunately, somewhere in the crosshairs of families deciding to choose vacation rentals over hotels, most owners failed to adopt the same red carpet service, convenience, amenities, quality and customer experience.

By adapting hotel principles to your own vacation rental business, you can stand out in what is becoming a very competitive, crowded marketplace.

What services do you offer that knock your guests’ socks off? Tell us about them in the comments section below.

Tyler Gillespie is the founder and CEO of Breakaway Vacation Rentals in Aspen, Colorado and the man behind, a blog where he shares his advice and observations from 10+ years in the vacation rental and travel industries.