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9. Travel in Packs

It’s no secret that traveling with friends is cost-effective—the larger the group, the less each has to pay. But finding a big enough base camp for everyone can be a thankless task. Which is why software developers Baer Tierkel and Mike Giles decided to launch otalo.com. “We thought it would be really helpful to have a single website that would search all the different vacation rental sites for you—there are hundreds out there—in a quick, easy way,” says Tierkel. Think Google, but for vacation homes. Another good resource is Vacation Rental by Owner, a favorite among second homeowners looking to rent out their dream houses (vrbo.com). Here you’ll find options like a brand-new cabin eight miles from Yellowstone ($1,500 a week; sleeps five) and an 18th-century villa in Argentina’s Sierras de Córdoba, close to mountain biking, trekking, and horseback riding galore ($2,400 a week; sleeps 12).

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