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Teresa Roebuck booked three business trips in a month and got the flights, hotels—and the $700 laptop computer—she wanted. By booking through a new site called Upside Travel, the education consultant was rewarded with $1,000 in gift cards and still figures she saved money for her company.

“I felt like I was cheating,” she says.

Upside is the new venture from Priceline founder Jay Walker backed by some big names in finance and…