"She's pretty on the inside": Hotels that need a second chance to make their first impressions

It's easy to see why a mediocre hotel would do everything in its power to spruce up its exterior: you only get one chance to make a first impression, after all. Exhibits A through Z? How about half the hotels in South Beach, where bright, inviting Art Deco buildings are a dime a dozen but where, if you don't pick the right one, you could end up in a place like this. What's surprising is how many hotels there are out there that seem as if they don't even try to invite you in in the first place. Granted, there's only so much you can do if you move into a building like this one. But come on, at least cover up a blemish or two with a billboard or something.

Take the Skyline Hotel in New York. It's located right off the Hudson Parkway, and indeed, from the street it could pass for a roadside motel. Even the font on the sign looks like it was pulled straight from an interstate motor lodge in Nevada. It's not until you step into the lobby that you breathe a sigh of relief and realize the Skyline is a hotel, and a decent one too. "You were surprised when you stepped into the lobby, weren't you?" one of the managers said to me when I interviewed her at the end of my stay. "That's what our guests always tell us." I was indeed. Pleasantly surprised. On the inside, the Skyline looks pretty much like many of its more expensive counterparts east of 10th Avenue. The marble floors in the lobby glimmer. There's a bell staff and a concierge. Throw in a bar and restaurant, a pool, and 231 rooms that often go for less than $200 a night, and the Skyline legitimately enters the conversation with midtown's myriad other midrange hotels.
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Dishonorable mention to two other huge big-city Hiltons with grotesque exteriors: the Hilton New York and the Capital Hilton in Washington, D.C., which looks like a hospital from the outside. The reason they're not on this list? Their interiors aren't particularly stylish either.