Where to stay in Fire Island
A car-free barrier island reached by ferry from Sayville, with two gay hamlets: the sleek, house-party Pines and the older, campier Cherry Grove. Hotel rooms are few, so book early for summer weekends, especially July 4th and Labor Day; the season runs roughly Memorial Day to late September.
The Grove Hotel
Ocean Walk, Cherry Grove
Cherry Grove's main hotel, with a pool, poolside bar, and the Ice Palace nightclub right on site. Adults only (21+); the best pick if you want to be in the middle of the Grove's drag shows and dancing.
Official siteBelvedere Guest House
Bayview Walk, Cherry Grove
A one-of-a-kind, Venetian-style guesthouse on the bay that calls itself a gay resort for men, with a pool, hot tub, gym, rooftop terrace and sunset bay deck. Rooms range from bay-view luxury to simple economy; some guests find the upkeep uneven, but the bayfront setting is unlike anywhere else on the island.
Official siteThe Madison Fire Island Pines
Fire Island Pines, near the harbor
A small boutique guesthouse a minute from the ferry and the ocean, with a heated pool, roof deck, and sun decks. The most comfortable hotel-style option in the Pines for a weekend of Low Tea and beach days.
Official sitePlan around these
Fire Island Leather Weekend
Fire Island Pines, NY · Dates TBA TBA, usually mid-May (2026 was May 15–17)
Early-season Pines weekend for the leather crowd.
Fire Island Season Opens
Fire Island Pines & Cherry Grove, NY · May 28–31, 2027
Memorial Day weekend: ferries go to summer schedules, Low Tea is back, shares move in.
Fire Island Bear Weekend
Fire Island Pines, NY · Dates TBA TBA, usually mid-June (2026 was Jun 11–15)
The Pines' bear weekend.
Invasion of the Pines
Cherry Grove → Fire Island Pines, NY · Jul 4, 2027
Every July 4 since 1976, the Grove's drag queens take a ferry to Pines Harbor and 'invade.' Free to watch.
Listings checked against official sites in 2025–26. Policies and prices change, so confirm before you book. We don't take money from hotels.