The cheapest months to visit St. Thomas in the U.S. Virgin Islands are September and October. This period falls during the peak of the Atlantic hurricane season, which naturally leads to a significant decrease in tourist traffic. Consequently, hotel rates drop to their lowest annual levels—often 30% to 50% cheaper than peak winter pricing—and many villas offer generous discounts to fill occupancy. While you face a higher risk of rain and tropical storms, the island is far less crowded, and local restaurants are more accessible. If the hurricane risk is a concern, the "shoulder season" months of May and June are excellent alternatives; they offer a balance of lower flight costs and beautiful weather before the humidity of late summer sets in. In 2026, savvy travelers are using travel insurance to mitigate the storm risk while taking advantage of these deep off-season savings.