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Kiawah Island Vacation Packages

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Kiawah Island Flight + Hotel Packages

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

Indigo Inn

3 out of 5
Price was $870, price is now $737 per person
$737
per person
Oct 30 - Nov 2
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Charleston (CHS)
Stay at this hotel in Charleston. Enjoy free breakfast, free WiFi, and 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 Ryder Hotel

The Ryder Hotel

3.5 out of 5
Price was $1,179, price is now $845 per person
$845
per person
Dec 19 - Dec 24
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.
Beautiful restaurant and wonderful coffee bar! Great pool service as well.

Reviewed on Sep 25, 2026

The Charleston Place

The Charleston Place

5 out of 5
Price was $1,075, price is now $828 per person
$828
per person
Dec 10 - Dec 12
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.
Everything was convenient. If getting room with balcony do not get street side

Reviewed on Sep 25, 2026

The Francis Marion Hotel

The Francis Marion Hotel

4 out of 5
Price was $1,001, price is now $771 per person
$771
per person
Oct 30 - Nov 2
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Charleston (CHS)
Book a stay at this luxury hotel in Charleston. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Charleston City Market and South Carolina Aquarium are located nearby.
Charming and authentic southern aristocratic feel. Great staff, superb value, ideal location. Room was spacious and comfortable and quiet. Highly recommended.

Reviewed on Sep 25, 2026

Water's Edge Inn - Adults Only

Water's Edge Inn - Adults Only

3.5 out of 5
Price was $983, price is now $765 per person
$765
per person
Dec 19 - Dec 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
Stay at this B&B in Folly Beach. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Folly Island Beaches and Folly River Park are located nearby.

The Pinch Hotel

The Pinch Hotel

4 out of 5
Price was $1,354, price is now $1,070 per person
$1,070
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
Book a stay at this spa hotel in Charleston. Enjoy free breakfast, free WiFi, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Charleston City Market and South Carolina Aquarium are located nearby.

The Ansonborough

The Ansonborough

4 out of 5
Price was $1,154, price is now $946 per person
$946
per person
Nov 27 - Dec 1
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.

The Inn At Middleton Place

The Inn At Middleton Place

3 out of 5
Price was $1,054, price is now $886 per person
$886
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charleston (CHS)
Book a stay at this family-friendly hotel in Charleston. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Middleton Place and Frankie's Fun Park are located nearby.
Very relaxing place to get away

Reviewed on Sep 24, 2026

Kiawah Island Vacation Packages 3-4 Night Stays

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

The Ryder Hotel

3.5 out of 5
Charleston Historic District
Price was $979, price is now $725 per person
$725
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
The Francis Marion Hotel

The Francis Marion Hotel

4 out of 5
Charleston Historic District
Price was $1,001, price is now $771 per person
$771
per person
Oct 30 - Nov 2
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Charleston (CHS)
Water's Edge Inn - Adults Only

Water's Edge Inn - Adults Only

3.5 out of 5
Price was $926, price is now $731 per person
$731
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
The Charleston Place

The Charleston Place

5 out of 5
Charleston Historic District
Price was $1,914, price is now $1,537 per person
$1,537
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)

Kiawah Island Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Water's Edge Inn - Adults Only

Water's Edge Inn - Adults Only

3.5 out of 5
Price was $983, price is now $765 per person
$765
per person
Dec 19 - Dec 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
The Ryder Hotel

The Ryder Hotel

3.5 out of 5
Charleston Historic District
Price was $1,179, price is now $845 per person
$845
per person
Dec 19 - Dec 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
The Francis Marion Hotel

The Francis Marion Hotel

4 out of 5
Charleston Historic District
Price was $1,205, price is now $939 per person
$939
per person
Dec 19 - Dec 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
The Ansonborough

The Ansonborough

4 out of 5
Charleston Historic District
Save 100% on your flight
Price was $1,504, price is now $1,182 per person
$1,182
per person
Dec 7 - Dec 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Breeze Airways
Fri, Dec 4 - Mon, Dec 7
SWF
Stewart Intl.
CHS
Charleston Intl.
$142 Roundtrip, found 1 day ago
$142
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Dec 4 from Stewart Intl. to Charleston Intl., returning Mon, Dec 7, priced at $142 found 1 day ago
Breeze Airways
Thu, Nov 12 - Sat, Nov 14
BDL
Bradley Intl.
CHS
Charleston Intl.
$190 Roundtrip, found 1 day ago
$190
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Nov 12 from Bradley Intl. to Charleston Intl., returning Sat, Nov 14, priced at $190 found 1 day ago
Delta
Tue, Oct 20 - Wed, Oct 28
JFK
John F. Kennedy Intl.
CHS
Charleston Intl.
$199 Roundtrip, found 20 hours ago
$199
Roundtrip
found 20 hours ago
Select Delta flight, departing Tue, Oct 20 from John F. Kennedy Intl. to Charleston Intl., returning Wed, Oct 28, priced at $199 found 20 hours ago
Delta
Sat, Oct 31 - Sat, Nov 14
BOS
Logan Intl.
CHS
Charleston Intl.
$199 Roundtrip, found 3 hours ago
$199
Roundtrip
found 3 hours ago
Select Delta flight, departing Sat, Oct 31 from Logan Intl. to Charleston Intl., returning Sat, Nov 14, priced at $199 found 3 hours ago