KAYAK: Featured in “Wedding Crashers,” this charming colonial mansion is a classy luxury resort — so dressing up like Rachel McAdams is probably tacky, creepy, and weird. http://on.kayak.com/PerryCabin
KAYAK: It’s ALL about the bar here. The rooftop bar gives you 360-degree views of the Manhattan skyline and in the summer they open their amazing pool. Outdoor cocktails and late-night swims? Can’t beat that
KAYAK: Once a prison, the hotel has a restaurant that even features original jail cells – so if you’re like us, you’ll enjoy pretending your butter knife is a really fancy shiv. on.kayak.com/LibertyBoston