If you are deciding on where to stay in Simpson Bay, there's a terrific assortment of suitable options. Expedia's booking page currently has 75 accommodation options within a 0.1-mile radius of downtown Simpson Bay.
You could investigate the Belmond La Samanna or the Four Seasons Resort and Residence Anguilla. The Belmond La Samanna is positioned 2 miles from the middle of Simpson Bay. The Four Seasons Resort and Residence Anguilla, is positioned 10 miles away. If you'd prefer, you could book a room at the CuisinArt Golf Resort & Spa or the Blue Pelican Vacation Rental.
6 miles from Simpson Bay you will find Grand Case, where you can explore Grand Case Beach and Octopus Diving. If you'd like to spend a night or two in Grand Case, check out the room rates at the Green Cay Villas and Riu Palace St Martin All Inclusive. 3 miles to the northeast of Simpson Bay, is Marigot, home to the Marquis Boutique Hotel and Sonesta Great Bay All Inclusive Beach Resort, Casino & Spa. While visiting Marigot, be sure to explore the Marigot Market and Fort St. Louis.