Hilton Head Island Chalets

We selected the 94 homes worth renting in this location

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Home spotlights in Hilton Head Island

Island Pines

Island Pines

  • 8 guests

  • 4 bedrooms

Hilton Head Island, Beaufort County

There is a certain kind of charm only found in the South, and this house has it in spades. Beautifully situated on the grounds of a vast private estate, surrounded by golf courses, and resting in the shadow of a stunning forest, this is an ideal spot for a restful and luxurious retreat for a family or a group of friends.

Oystercatcher

Oystercatcher

  • 6 guests

  • 2 bedrooms

Hilton Head Island, Beaufort County

There’s a real sense of calm about this newly remodelled beach house. Whether it’s the neutral shades, or the copious amounts of natural light, you’ll find any tension melting away the minute you step through the door.

Summer Duck

Summer Duck

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

On a picturesque street of swaying palm trees sits this traditional Victorian home. Built in 1885, it has a square, symmetrical exterior, covered porches, high ceilings and exposed beams.

Checkered

Checkered

  • 10 guests

  • 5 bedrooms

Cannonborough Elliotborough, Charleston

Spanning two floors, this elegant home embraces its historic setting while offering 21st-century luxuries. Warm and welcoming from the moment you arrive, you'll find a whitewashed living area with contrasting window frames, dining chairs and accent tables.


We selected the top 3% holiday homes in Hilton Head Island Chalets

Explore the 94 most perfect homes in our collection

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Most popular homes in Hilton Head Island

Fairway Breeze

Fairway Breeze

  • 9 guests

  • 4 bedrooms

Hilton Head Island, Beaufort County

Charming Urban Oasis

Charming Urban Oasis

  • 3 guests

  • 1 bedrooms

North Historic District, Savannah

Rocking Chair Residence

Rocking Chair Residence

  • 20 guests

  • 10 bedrooms

Cannonborough Elliotborough, Charleston

Wicker

Wicker

  • 12 guests

  • 4 bedrooms

Hilton Head Island, Beaufort County

Rockfish

Rockfish

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Cotillion

Cotillion

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Singing Sweet Carolina

Singing Sweet Carolina

  • 12 guests

  • 6 bedrooms

Hilton Head Island, Beaufort County

Smoke on the Water

Smoke on the Water

  • 12 guests

  • 4 bedrooms

Hilton Head Island, Beaufort County

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Frequently asked questions

A chalet in Hilton Head Island, Beaufort County, South Carolina, United States is the perfect accommodation for a cosy holiday. Find your dream one by browsing Plum Guide’s collection of homes. They come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book today and enjoy a short or extended stay in the most charming chalets that Hilton Head Island, Beaufort County, South Carolina, United States has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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