Samantha Gillingham Appointed Director of Sales at Jayne’s Luxury Rentals
by Marsha Mowers
Samantha Gillingham has joined Jayne’s Luxury Travel as Director of Sales and Business Development.
It’s a new year, new start for advisor favourite Samantha Gillingham as she begins her new role today as Director of Sales and Business Development at Jayne’s Luxury Rentals.
The company offers a novel vacation alternative that integrates owner-rental properties with a five-star luxury experience. It provides guests the opportunity to stay in cottages, chalets, or villas located in prestigious destinations such as Whistler, BC, and Muskoka,ON.
There are currently 269 properties available, 200 of which are lakefront, with an average booking of $46,700, length of stay 13 days and an ADR of $3648 CDN per day. Jayne’s also has a very high repeat guest rate, with more than 70%.
Extending her existing relationships with advisors and developing new ones will be a top priority for Gillingham in her new role. She will be attending premier international trade shows including ILTM and LE Miami to build relationships with top travel agencies, tour operators, and luxury consortia such as Virtuoso and Signature Travel Network.
Gillingham will also manage agency relationships in North America, including training, marketing support, and exclusive partnerships. Regular sales trips to key markets like New York and Los Angeles, along with hosting her signature Fam trips to Muskoka for top travel advisors, will be prioritized.
“I’m beyond excited to step into my new role as Director of Sales & Business Development at Jayne’s Luxury Rentals,” Gillingham told Travel Market Report Canada last week. “Having had the opportunity to grow up in the stunning Muskoka region, I’ve always had a deep love for this world-class destination, and now I get to combine that passion with my sales expertise to help elevate Jayne’s to new heights.
With my extensive background in luxury travel and key industry relationships, I’m ready to bring fresh opportunities to travel advisors and introduce even more discerning clients to the unparalleled beauty and exclusivity of Jayne’s curated properties. This is more than just a job—it’s an incredible opportunity to redefine ultra-luxury rentals in Muskoka and beyond.
I can’t wait to hit the ground running and help showcase everything that makes Jayne’s the ultimate choice for high-end travellers,” she added.
“Let’s make waves in the luxury market.”

