Chincoteague (VA) and Assateague (MD) are fairly small areas so visiting in the shoulder seasons or winter can be worth it.
Assateague Island National Seashore is part of the National Park Service (NPS) so plan to bike or walk to avoid the fees. Or snag an annual pass which also works for Shenandoah National Park!
Choose from hotels, bed and breakfast, and home share options - many with great water views.
Restaurants can be crowded in the summer but it can be easier to get reservations at fancy spots like waterfront Etta's
You can also enjoy dinner or a drink with your toes in the sand at Ropewalk. Nothing beats a table right on the sandy beach.