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Hilton Head Island Getaway (Self Drive)

4 to 6+ Nights from $1,359*
* Sample price: Priced within the past 7 days for a 8/5/2025 arrival, departing New York City NYC (All Airports) (NY), US. Choose departure city, cabin and dates.

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This 4 night sample itinerary includes:

  • Flight into and out of Hilton Head Island
  • Rental Car for 5 days
  • Hotel for 4 nights in Hilton Head Island

Explore South Carolina and its beautiful surrounding cities with many activities, night life and much more with a Rental Car. Visit Hilton Head Island a resort island famous for its incredible beaches and its world-class golf courses. Offers a relaxing, laid-back and welcoming vibe and beautiful beaches and golf courses.

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support

Flexible Itinerary

  • Hilton Head Island, SC

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Trip Summary

  • Hilton Head Island, SC
    Hilton Head Island, SC

    Hilton Head Island is America`s favorite island, consistently ranked one of the top Islands in the United States, offering 12 miles of pristine beaches and everything you need for the ultimate retreat. It`s famous for its world-class golf courses, its exceptional restaurants, and its high-energy water sports. Every year between May and October, sea turtles visit the beaches of Hilton Head. They lay hundreds of nests and thousands of hatchlings are born. From sunrise to sunset, you will want to cherish every moment on this magical Island because Hilton Head has it all.

    Explore The Harbor Town Lighthouse, the Coligny Beach Park, the Hilton Head Island Beach, the Fort Pulaski National Monument, the Coastal Discovery Museum, the Pinckney Island National Wildlife Refuge, the Harbor Town Golf Links, the Pinckney Island and so much more!

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