No day trips out to Montauk would be complete without at least one night in this iconic (and rather massive) respite at the end of the world. Following a multimillion-dollar renovation, Gurney’s is back in action with stunning guest rooms, noteworthy dining and drinking across five venues (from the well-respected LDV Hospitality), and a private oceanfront that’s fit for even the most discerning beach bum. You've also got Hither Hills State Park and a great golf course a small drive away.
Best for: Relaxing to the max in front of ocean views.
Price range? Expensive.
Time Out tip: The full-service spa has a seawater pool and sauna.