Jennifer Whaling turned her passion for hospitality into CottageStays, a thriving vacation rental business in Ontario’s cottage country. What started with a single lakefront property has grown to over 50 homes, all managed with the help of her incredible team and a shared commitment to helping guests "Make Your Memories Happen."

Can you tell us a little bit about your history?

CottageStays started, like so many great things, with a mix of passion, necessity, and just a touch of frustration. My journey here has been anything but traditional!

What is your background?

I’ve worn many hats in my life: municipal administration, tech (working on property tax software), farming, bookkeeping, and full-time mom life. When we started winding down our farming activities, we wanted to invest in a rental property. But long-term rentals? No, thank you! The landlord tenant laws here are wild, I couldn’t stomach the idea of someone not paying rent, trashing the place with five dogs, and my hands being tied. So, we pivoted to short term rentals.

We bought a beautiful lakefront cottage, something we could both enjoy and invest in. At first, we used a cottage rental agency, but I quickly realized: I could do this better. Then my cousin bought a cottage, then a neighbor… and before I knew it, I was managing five cottages in my first year! That’s when I knew I needed serious software to scale while still delivering a personal touch, enter OwnerRez.

As CottageStays grew my first hire was Lea, our reservationist and 'boots on the ground.' She had the perfect “Grandma” look, which came in handy when guests needed a gentle nudge. Picture this: monster trucks parked all over the lawn, Lea shows up, sweet as can be, and suddenly, those trucks are gone with zero drama. Because, honestly, who’s going to be mad at Grandma?

Then came Shauna, our Guest Services guru, reservationist, and marketing whiz. She’s a Jack of All Trades, literally. She also represents a different generation of travelers, which has been a game changer. Lesson learned: always hire someone different from yourself! On changeover day, she’s the master puppeteer, managing all guest communication while Brenda and I are on the road, fixing issues, supporting housekeepers, and making sure everything runs smoothly.

Speaking of Brenda, she stepped into Lea’s role last year and has been a rock for our housekeeping team. She has a "can do" attitude, which is a lifesaver when our day goes sideways (because, let’s be real, it happens a lot!). No matter what comes up, she tackles it head on and keeps everything running smoothly.

Let’s be real, this is a high stress job in a stunning location. We’re in the business of creating the backdrop for lifelong memories, which is why our tagline is: "Make Your Memories Happen." But let’s not forget, it doesn’t happen without an incredible team including an army of housekeepers who tackle all the behind the scenes chaos and garbage.

Are you from the geographical area where your properties are located, or did you move there later?

I grew up here and returned when we started our family. I live just 15 minutes from our own cottage, and all the properties I manage are within a 30 minute radius of my home. That way, if a toaster breaks, I can be there in person because no one wants to start their vacation without toast!

What do you love the most about the vacation rental business?

Honestly? The chance to help families make lifelong memories. There’s something special about knowing we’re providing the backdrop for those moments, kids catching their first fish, sunset bonfires, dogs splashing in the lake.

It’s also the perfect mix of left brain and right brain work. One minute, I’m deep into numbers, organization, and problem solving, and the next, I’m creating marketing campaigns and engaging with guests. No day is ever the same!! It’s never boring, that’s for sure!

What do you dislike the most about it?

Fraudsters. The guests who try to scam a refund for no good reason drive me nuts. And ironically, the ones who do have an issue rarely complain or let us fix it.

Regulations can also be a challenge, but my background in municipal administration gives me a different perspective. I know councillors are our representatives, not the enemy, so I take the time to talk with them and build relationships. That approach has earned me a lot of respect in the community, which helps in shaping fair policies.

How do you use OwnerRez to manage your business?

Most everything pretty much. OwnerRez is the Hub of our business, from our marketing and website, to our reservation staff, guest services, housekeeping, maintenance, hot tub, snow removal and more. And of course our financials which is the whole point LOL. Most of our guest communication happens through OwnerRez with SMS and channel messages. We also integrate with a contact manager for email marketing, which fully syncs with OwnerRez (super cool, considering I used to sell Contact Managers!).

We use OwnerRez widgets on our website, linking to Google Analytics so we can fine tune our marketing. If someone starts booking but doesn’t finish, OwnerRez automatically emails us: “NAME has started Book Now,” giving us a chance to reach out and assist before they move on. OwnerRez links with PriceLabs exactly how I want it to and we have seasons setup as a backup. OwnerRez links with OpertoTeams our housekeeping/maintenance program creating all cleaning tasks, hot tub checks, and SNOW removal which has been a challenge this year ugghhh. Last week the roads were closed for 4 days and we had guests stuck up to 3 days longer than they expected.

When a booking is made, all the triggers kick in to collect security deposits, send rental agreements, send packing lists, rent linens, rent paddle boards/lake mats. And despite being a tiny company, just two of us working full time, we run like a much bigger operation. I see other companies my size with five full time staff members. Thanks to OwnerRez, we can stay small but mighty while still offering personalized service, like lavender gifts for couples or homemade dog treats with a handwritten note.

And the accounting integration? Absolute lifesaver. Invoices and deposits are automatically entered into our accounting software, and OwnerRez reporting lets me track revenue trends which is phenomenal. Now I can see that for March break this year we are doing way better than last year.

What is the most useful feature OwnerRez offers?

I love the automation, triggers, SMS, and channel messages. They make guest communication seamless. My latest trigger emails my head housekeeper a reminder 7 days prior to guest arrival (when there is only 2 guests) to schedule a Lavender gift (lavender bubble bath and a lavender sachet). My favorite SMS text is the one that goes out to guests who have a dog. This text goes out on day three of their stay:

"Hey DOGNAME🐾
Hope you're having a blast at COTTAGENAME!
Would you mind sharing a paw-some pic with us? We'd be thrilled to feature you on our social media pages! Just send us a pic or tag us @cottagestays on Facebook/Instagram...and maybe they will make it to our social media page
Can't wait to see your adorable face! 📸😊"

I originally asked people to tag us on Facebook and Instagram, but no one does. Then I asked people to share a picture of the sunset; we have the Top 10 sunsets in the world here. After that, around 10pm my phone would blow up with photos. That's not the engagement I wanted. Then I started asking for dog photos. Game changer. Guests love sharing, their friends engage like crazy, and our social media reach skyrocketed.

We also have triggers set up for garbage pickup day. It's a bit clunky, but it works. And our message again is fun:

"Thanks for being eco-friendly legends! 🌿♻️
Garbage day is tomorrow Monday - Please put garbage and recycling bins at the end of the lane on THIS side of the road Sunday evening or early Monday morning.
Please bring in after they have been picked up or let us know if you will be away.
Here is a helpful guide to what can go in your recycling container:
https://www.bra.org/material-guide/recycle-in-your-bluebox/
We do not have green bin pickup at this time
Have a Trash-Tastic evening LOL"

And we just implemented a guest AI (HostBuddy) which communicates right in my OwnerRez inbox so we can see all the guest communications. This will hopefully alleviate some work off of Shauna's plate, but also means guests can receive answers in the middle of the night. Shauna didn't want to work 24hrs a day for some reason?? LOL

Now managing over 50 cottages, CottageStays is known for personal touches, exceptional service, and its mission to help guests "Make Your Memories Happen." With OwnerRez powering her operation, Jennifer continues to grow while keeping her focus on the guest experience. We are excited to see her business continue to deliver amazing stays!