Samantha Gillingham exits Club Med, joins Jayne’s Luxury Rentals as dir. of sales & biz development

From all-inclusive resorts to luxury cottages.

Travel pro Samantha Gillingham has made a bold career move, leaving her role as a business development manager at Club Med for a new challenge in Ontario’s cottage country.

Gillingham tells PAX that she is now director of sales and business development at Jayne’s Luxury Rentals, a cottage rental and concierge service that boasts a portfolio of eye-popping vacation properties primarily in Muskoka, but also in Toronto, the Kawarthas, Haliburton, the Collingwood area, all the way to Whistler, B.C.

In her new role, Gillingham, who starts at the company today (March 3), will lead Jayne’s global business development, expanding its presence in the luxury market by working with the travel trade.

Her responsibilities include driving revenue growth through targeted sales strategies, overseeing the inside sales team, and managing key industry relationships, including Dominique Debay’s third-party representation agency, attending roadshows, and representing Jayne’s at luxury travel trade shows, such as ILTM and LE Miami.

Gillingham will also oversee agency relationships across North America and conduct sales trips to major markets within Canada and the United States, positioning Muskoka as a top-tier ultra-luxury destination.

“From childhood summers on the lake to a career in luxury travel, my love for Muskoka has been lifelong. I truly admire how Jayne’s Luxury Rentals has transformed the vacation rental space in Canada, curating an incredible portfolio of stunning lakefront properties—all just 2.5 hours from Toronto,” Gillingham tells PAX, saying she’s “thrilled” to put Muskoka and other beautiful regions “on the global luxury map.”

Canadian luxury

For the past 10 years, Jayne’s Luxury Rentals has emerged as a leader in the high-end vacation rental space, earning recognition in Forbes Magazine and winning the prestigious RBC Canadian Women Award for Entrepreneurship and the Globe and Mails Top Growing companies.

Unlike traditional rental platforms, Jayne’s operates to ensure full control over the guest experience. From a dedicated concierge team to an in-house cleaning staff, every detail aims to provide a five-star service. During peak season, the company will employ a workforce of up to 85 professionals.

And upscale vacations live here. Of Jayne’s 269 properties, 200 of them are lakefront, while the average booking comes in $46,700. The average length of stay, meanwhile, is 12.8 days, with an ADR of $3,648 per day.

It has a loyal client base, too. The company says it has a repeat guest rate of more than 70 per cent.

This premium segment is where Gillingham sees big opportunities.

“Through conversations with top travel advisors, I’ve seen firsthand how Jayne’s is redefining the ultra-luxury experience,” she said. “As someone who is passionate about sales, travel, and showcasing Canada’s beauty, I believe it’s time for Muskoka to take its place among the world’s premier luxury getaways.”

“I can’t wait to connect with travel professionals, introduce them to Jayne’s, and help bring even more discerning travellers to this extraordinary region.”

Gillingham said 75 per cent of Jayne’s Luxury Rentals’ clientele is Canadian.

“Now, we’re focused on elevating Canada’s place in the global luxury travel market—not competing with domestic offerings, but standing alongside the world’s most sought-after destinations,” she said. “With its stunning natural landscapes, pristine lakes, and exclusive properties, Muskoka is truly a world-class retreat.”

“Jayne’s commitment to excellence sets us apart, and I’m eager to work with industry partners to bring more global luxury travellers to Muskoka.”

#SamsFAMs will continue

Her message to the travel trade community?

“I’m still here to support them every step of the way!” Gillingham said. “As I step into this new role, my goal is to make the booking process seamless and provide you with an exciting new product to add to your portfolio.”

“It’s time to put Muskoka on the luxury travel map and shift your clients’ focus to the incredible destinations right in their own backyard. Canada deserves a bigger spotlight in the global luxury space, and Muskoka is the perfect place to start.”

“#SamsFAMs” will also continue, said Gillingham, who invites travel advisors to discover the properties of Jayne’s Luxury Rentals firsthand.

“Let’s discover Muskoka together and show the world just how extraordinary Canadian luxury can be,” she said.

Samantha Gillingham can now be reached at 647.654.6106 and at  samantha@jaynesluxuryrentals.com.

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