Mohegan Sun Casino, CT

Where to stay: Feeling lucky? Head to the Mohegan Sun casino. Don’t forget to ask for their Legendary Escape Package, which starts at $200 per night.
Getting there: Board the Metro-North train from Grand Central, get off at the New Haven train station, and then hop on a bus to get to the casino in Uncasville, Connecticut. You’ll be there in under three hours.
What to do: If you're not big on gambling, enjoy the nightlife after dining at a top restaurant.
Grand total: $540 per couple for two nights and transportation -- but just think about the prize money awaiting you at the slots!