1. Montauk Manor
At this condominium resort hotel, 100 rental units are available for a stay on Signal Hill, Montauk’s second-highest point. The property’s got a neat backstory, too: It opened in 1927 by Fisher, an industrialist who wanted to make Montauk a summer getaway. Nowadays, guests have access to heated indoor and outdoor swimming pools (the latter is open from Memorial Day to Columbus Day, weather permitting), a day spa, three tennis courts, a small gym and an on-site restaurant, Monte's at The Manor (schedule varies; check on seasonal availability). Daily maid service is also offered. Choose between studio apartments or one-, two- or three-bedroom suites.
Time Out tip: A courtesy van can get you around, just put in a request beforehand.