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Kiawah Island Vacation Packages

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A large, sprawling tree with extensive branches and dense green foliage in a forested area.

Kiawah Island
South Carolina
United States of America
North America
Hotwire.com

Kiawah Island Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.

Club Wyndham Ocean Ridge

3.5 out of 5

Price was $1,634, price is now $1,266 per person

$1,266

per person

Dec 27 - Jan 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Charleston (CHS)

Book a stay at this golf hotel in Edisto Island. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Edisto Beach State Park and Botany Bay Plantation Heritage Preserve and Wildlife Management Area are located nearby.

The room was clean and spacious for 2 people. Loved renting bikes and riding the paths the island has. It's NICE & QUIET. If you're looking for alot of action you need to go somewhere else. It's a layed back family beach. Hope it can stay that way. FYI...... their is a sale pitch for the time share buy in. JUST SAY NO!

Reviewed on May 22, 2026

The Ryder Hotel

3.5 out of 5

Save 100% on your flight

Price was $2,127, price is now $1,427 per person

$1,427

per person

Dec 27 - Jan 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Charleston (CHS)

Stay at this hotel in Charleston. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Charleston City Market and Waterfront Park are located nearby.

The Charleston Place

5 out of 5

Save 100% on your flight

Price was $4,335, price is now $3,207 per person

$3,207

per person

Dec 27 - Jan 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Charleston (CHS)

Book a stay at this luxury hotel in Charleston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Charleston City Market and Waterfront Park are located nearby.

To have a luxury hotel like this that is privately owned and not a massive corporate feel is awesome. We love the Charleston place and all the changes they have been making over the past few years. Beautiful property great vibe and quiet luxury.

Reviewed on Oct 18, 2026

Emeline

4 out of 5

Price was $2,223, price is now $1,666 per person

$1,666

per person

Dec 27 - Jan 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Charleston (CHS)

Book a stay at this luxury hotel in Charleston. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Charleston City Market and Waterfront Park are located nearby.

The Ansonborough

4 out of 5

Save 100% on your flight

Price was $2,648, price is now $2,044 per person

$2,044

per person

Dec 27 - Jan 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Charleston (CHS)

Book a stay at this business-friendly hotel in Charleston. Enjoy free breakfast, free WiFi, and a rooftop terrace. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Charleston City Market and Waterfront Park are located nearby.

Andrew Pinckney Inn

4 out of 5

Price was $2,051, price is now $1,635 per person

$1,635

per person

Dec 27 - Jan 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Charleston (CHS)

Book a stay at this business-friendly hotel in Charleston. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Charleston City Market and Waterfront Park are located nearby.

The Restoration

4 out of 5

Price was $2,245, price is now $1,801 per person

$1,801

per person

Dec 27 - Jan 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Charleston (CHS)

Book a stay at this luxury hotel in Charleston. Enjoy free breakfast, free WiFi, and a rooftop terrace. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Charleston City Market and Waterfront Park are located nearby.

The property needs maintenance, staff need help.

Reviewed on Oct 19, 2026

Elliott House Inn

4 out of 5

Price was $1,612, price is now $1,294 per person

$1,294

per person

Dec 26 - Dec 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Charleston (CHS)

Stay at this guesthouse in Charleston. Enjoy free WiFi, room service, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Charleston City Market and Waterfront Park are located nearby.