Nine places to sleep, one honest question for each: who is it right for, and what is the catch? This page lays out every area we cover, pulled straight from our area guides, so you can find your base in one scroll.
If you are still deciding between the two countries that share this island, start one step back with which side should you stay on. Once you have a side in mind, the areas below narrow it down.
At a glance, by traveler type
- Nightlife and convenience: Simpson Bay or Maho, walkable bars and casinos near the airport.
- Food and romance: Grand Case, the island’s dining street, calm and low-key.
- Quiet and seclusion: Anse Marcel, Cupecoy, or Oyster Pond, all trading convenience for calm.
- Families and beach days: the calmer north end of Orient Bay, or convenient Simpson Bay.
- A cruise day in port: Philipsburg, where you dock and where the shopping is.
- French cafe culture: Marigot, markets, patisseries, and the Anguilla ferry.
- On a budget: the Dutch side generally, with more mid-range lodging and groceries around Simpson Bay and Philipsburg.
The one rule that makes all of this easier: the border is open, so wherever you sleep, the rest of the island is a short drive away. You are choosing your home base, not your whole trip.
Every area, honestly compared
Each area below comes straight from our full area guides, verdict and tradeoffs included. Tap through for the long version, the getting-there notes, and the local detail.
Anse Marcel
French sideA secluded resort cove up north, calm and quiet, and a long way from the action
Best for
Know before you book
Cupecoy
Dutch sideClifftop condos, big sunsets, and a beach that comes and goes with the tide
Best for
Know before you book
Grand Case
French sideThe island's food street, from beachfront lolos to white-tablecloth French dining
Best for
Know before you book
Maho & Mullet Bay
Dutch sideJets overhead, casinos at night, and the island's favorite beach next door
Best for
Know before you book
Marigot
French sideThe French-side capital: market mornings, harbor cafes, and the ferry to Anguilla
Best for
Know before you book
Orient Bay
French sideA long, lively beach of clubs and watersports, with wind, waves, and seaweed in season
Best for
Know before you book
Oyster Pond
BorderA quiet marina on the border, minutes from Dawn Beach and far from everything else
Best for
Know before you book
Philipsburg
Dutch sideThe cruise-port capital: duty-free shopping, a beach boardwalk, and cruise-day crowds
Best for
Know before you book
Simpson Bay
Dutch sideMarinas, a strip of restaurants and bars, and planes on approach overhead
Best for
Know before you book
Booking a room
The hotel links in each section point to Booking.com and Expedia. A few of those will become affiliate links once the partnerships are approved, which means a booking could pay us a small commission at no extra cost to you. That never buys a spot on this page: the areas are ranked on merit, and the tradeoffs above are the same ones we would tell a friend. See our affiliate disclosure for how that works.
Still weighing the bigger question of Dutch side versus French side? Read which side should you stay on next.
