Vacations can be tricky: It’s often an adventure to a new place where one expects to stay at a great hotel or inn that. But what if you’ve decided to take part in the share economy and book through Airbnb? The global hosting giant has turned the hospitality industry on its head, capitalizing on an age where personalized service ranks right up there with traditional, and where entrepreneurs—like the founders of Airbnb—have figured out that the next great business idea may require nothing more than a simple double take on an old one.

The relaxed nature of the Airbnb model though leaves the door open—quite literally—for error, read: lost keys or a potential lack of home security: no daily linen service or little soaps in the bathroom: disheveled, unattractive environs: or, especially, a lack of guidance when it comes to navigating a new destination.

This same line of thinking occurred to Gillian Harding. The Hamptons resident and style maven saw a dearth in the housing market three years ago when it came to luxury accommodations. After listing her own home on Airbnb and, soon thereafter, meeting the firm’s owners at a party in San Francisco, Harding had a thought: What if guests could check in with someone who took care of their every need? With that, Checkkin was born, a business that welcomes guests booking homes through Airbnb. She now takes on the task of listing a residence, creating their story on the Airbnb site, greeting clients, and looking after their every need.

Harding started her company where she resides—on the East End, one of the most sought-after vacation destinations around. The market is ready-made for the investment bankers, Wall Street executives, and the cadre of wealthy individuals she regularly attracts as clientele. Checkkin also offers a concierge service, booking private planes, sea planes, or helicopters from Manhattan or LaGuardia and virtually any other need from a guest’s initial booking to their departure. Harding outfits each home with sumptuous white Frette bedding and beautiful candles and fragrances from Antica, and provides guests with a welcome gift—a bottle of her own line of wine made by one of the oldest vineyards in France. It’s something she started this summer—Muscadat by Checkkin, thinking it best to expand her brand with something very special. “So many people have experienced our new vintage!” she says of the bottles made exclusively for her company. “It will be available in area wine shops by end of year, and we’re now in talks to develop a chardonnay, rose, and merlot as well.”

Checkkin will take this exclusivity a step further with their ultra-premium service, Checkkin Select, for the top one percent checking into high-end Hamptons homes. Besides staging the residences, Select garners staff, like private chefs, and services, such as transportation to and from a client’s Blade Helicopter or ExcelAire Jet. Dan Kahn, Vice President of Charter Sales for ExcelAire the private jet company that works closely with Harding to deliver top level service to the wealthy business people and families they serve, notes that Harding is the consummate professional. “She can almost predict what clients require and makes sure every request is attended to, which falls in line with our philosophy. For us, ‘no’ is never an answer,” he says. “We’re also in constant communication, especially in the summer in the Hamptons. Working with Gillian is just a pleasure—she’s a great person. It’s almost not work!”

Airbnb is also planning to step into the luxury market this year with the launch of Airbnb Lux, a more sophisticated arm of the business catering to those with unlimited budgets. “Because we’re already in that market, we’re positioned in the right place for the launch of Airbnb Lux—and some are already experiencing its services,” Harding adds. “Beyonce stayed at a $10,000-a-night Airbnb Lux for her recent Superbowl performance.”

Despite running Beta testing in the Hamptons market, Harding plans to set up in other locales around the U.S. and internationally next year. Her clientele is a jet set one already, with those wanting to recharge looking to experts like Harding to help.

“It’s very important that guests meet someone instead of arriving in the dark and foraging for a key in a mailbox,” says the entrepreneur, who had a successful interior design business as well as fashion company prior to her hospitality venture. “It makes them feel right at home. What moves her most though is the way Airbnb is transforming lives. Harding met a 90-year-old gentleman in her neighborhood, a Mr. Frederick Brown, who owned a beach cottage in Sag Harbor that had been shuttered for 25 years. When Harding told him about her relationship with Airbnb, and that she could make him a handsome profit, Brown had the house fixed from top to bottom—including redecoration—and had Harding promptly list it. His cottage is now part of the Airbnb community, to the tune of $400 dollars a night. “What Airbnb is doing for the older generation is incredible,” he says. “It’s giving us the financial freedom to enjoy our final years. At 90, I’m an Airbnb host and loving it!”

Harding realizes that guests never know what to expect in a new place. “Having someone plan everything is crucial,” says the Trinidad native who utilizes her interior design background for staging, and has a line of towels, bedding, and Checkkin magazine on the horizon. “We offer bespoke experiences and five-star-services to the host and guest,” says Harding. “They’re taking a closer look at how booking a luxury home could compare to booking a high-end suite at a five-star hotel. We’re changing the way the one percent vacations.”



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