Book Luxury Winter Rentals in Charleston

We selected the 90 homes worth renting in this location

Who's coming along?

Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

An extra fee may apply

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Home spotlights in Charleston

Swing Kings

Swing Kings

  • 8 guests

  • 4 bedrooms

Radcliffeborough, Charleston

With its white clapboard exterior and powder-blue window shutters, this traditional home is the belle of the ball in Charleston. Step into a Southern scene of four-poster beds, floral wallpaper and palm prints in each of the bedrooms.

Rocking Chair Residence

Rocking Chair Residence

  • 20 guests

  • 10 bedrooms

Cannonborough Elliotborough, Charleston

This historic home has been beautifully brought to life by its Charleston-native hosts. Immediately you’re welcomed by the traditional panelled exterior, the polished beams and hardwood floors that run throughout.

Lime Green Wish

Lime Green Wish

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Neatly tucked away at the back of the lot, this picturesque home offers privacy from the main road. Even as you approach, you’ll be smitten with the Southern characteristics that define it.

Southern Charm

Southern Charm

  • 10 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Embracing past and present, as all Charleston homes should, a careful balance of contemporary southern living with traditional features gives this home an elegant feel. Featuring beautiful hardwood floors, exposed beams and customary shutters, you’ll feel grounded in this historic location.


We selected the top 3% holiday homes in Charleston Vacation Rentals for Winter

Explore the 90 most perfect homes in our collection

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Most popular homes in Charleston

Checkered

Checkered

  • 10 guests

  • 5 bedrooms

Cannonborough Elliotborough, Charleston

Square Dance

Square Dance

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Ain't She Sweet

Ain't She Sweet

  • 16 guests

  • 8 bedrooms

Cannonborough Elliotborough, Charleston

Carolina Wren

Carolina Wren

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Cotillion

Cotillion

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Dixie Chic

Dixie Chic

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Summer Duck

Summer Duck

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Hominy

Hominy

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

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Check upcoming rates & availability for Charleston Vacation Rentals for Winter


Frequently asked questions

Browse our remarkable collection of luxury Vacation Rentals for Winter in Charleston, Charleston County, South Carolina, United States. As only the top 3% of homes go on to become Plum Award winners, you can be certain that your chosen home will be ideal for you. Each home in our range must pass 3 rounds of testing, and comes fully furnished with a well-equipped kitchen, all linen, and essential bathroom toiletries included. Make the most of the chilly season, and wrap up warm in a comfortable Winter Holiday Rental in Charleston. Reach out to our caring team of experts, who love nothing more than helping you discover the perfect home for your trip.

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