Unless you’re a business traveler or live in a hotel a la Eloise, earning enough points for a free night’s hotel stay can feel like a, pardon the pun, pointless effort. Typically, most repeat guests don’t reap the rewards of a hotel loyalty program until after they’ve completed 10–15 stays. (Fine print: That’s stays, not nights.) While there are many ways to earn points aside from booking a room—by having a hotel-branded credit card or by signing up for the program’s earning promotion of the month—you’ll still have to deal with blackout dates, expiration dates, and unexpected “restructurings” of the points-earning system. Playing the points game also forces you to stick to chain hotels that look indistinguishable from one another, even though they might be at opposite ends of the world. But booking a cool boutique hotel that doesn’t offer perks for your repeat visits can also leave you feeling empty inside.

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