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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 $650, price is now $510 per person
$510
per person
Oct 25 - Oct 28
found 10 hours ago
Roundtrip flight included
Philadelphia (PHL) 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
Save 100% on your flight
Price was $1,928, price is now $1,223 per person
$1,223
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip non-stop 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

The Charleston Place

5 out of 5
Save 100% on your flight
Price was $2,052, price is now $1,436 per person
$1,436
per person
Oct 12 - Oct 16
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.
The Charleston Place hotel has great food and service. The Bar, is a great place to hang out with such fantastic service and food. Room services also go way out of there way to assist you. Love staying here.

Reviewed on Aug 24, 2026

Water's Edge Inn - Adults Only

Water's Edge Inn - Adults Only

3.5 out of 5
Price was $807, price is now $587 per person
$587
per person
Oct 12 - Oct 16
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.
Nice place, walking distance to the beach, restaurants, and shopping but they also will shuttle you over if needed. Room was clean and comfortable, staff was very helpful, enjoyed afternoon happy hour and morning breakfast. Would stay again.

Reviewed on Aug 23, 2026

137 Grand Pavilion by Avantstay Steps to Beach + Resort Pools Wild Dunes Gated

137 Grand Pavilion by Avantstay Steps to Beach + Resort Pools Wild Dunes Gated

3 out of 5
Save 100% on your flight
Price was $2,648, price is now $1,986 per person
$1,986
per person
Oct 12 - Oct 17
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
Stay at this cottage in Isle of Palms. Enjoy free parking, a beach locale, and balconies. Popular attractions Wild Dunes Resort Golf Course and Isle of Palms Beach are located nearby.

Andrew Pinckney Inn

Andrew Pinckney Inn

4 out of 5
Price was $1,196, price is now $907 per person
$907
per person
Oct 12 - Oct 16
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.

Oceanfront w/ Pool, Panoramic Deck Views, 5bdr Folly Ocean Breeze by Avantstay

Oceanfront w/ Pool, Panoramic Deck Views, 5bdr Folly Ocean Breeze by Avantstay

3 out of 5
Save 100% on your flight
Price was $2,704, price is now $2,104 per person
$2,104
per person
Oct 18 - Oct 21
found 1 hour ago
Roundtrip flight included
Philadelphia (PHL) to Charleston (CHS)
Book a stay at this beach cottage in Folly Beach. Enjoy free parking, a beach locale, and balconies. Popular attractions Folly Island Beaches and Lighthouse Inlet Heritage Preserve are located nearby.

Poseidon By Avantstay On The Beach! Two Ocean Facing Balconies & Hot Tub

Poseidon By Avantstay On The Beach! Two Ocean Facing Balconies & Hot Tub

3.5 out of 5
Save 100% on your flight
Price was $1,868, price is now $1,458 per person
$1,458
per person
Oct 18 - Oct 21
found 1 hour ago
Roundtrip flight included
Philadelphia (PHL) to Charleston (CHS)
Stay at this cottage in Folly Beach. Enjoy free parking, a beach locale, and concierge services. Popular attractions Folly Island Beaches and Center Street are located nearby.

Kiawah Island Vacation Packages 3-4 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 $807, price is now $587 per person
$587
per person
Oct 12 - Oct 16
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
Save 100% on your flight
Price was $1,928, price is now $1,223 per person
$1,223
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charleston (CHS)
The Charleston Place

The Charleston Place

5 out of 5
Charleston Historic District
Save 100% on your flight
Price was $2,052, price is now $1,436 per person
$1,436
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
Andrew Pinckney Inn

Andrew Pinckney Inn

4 out of 5
Charleston Historic District
Price was $1,196, price is now $907 per person
$907
per person
Oct 12 - Oct 16
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.
Holiday Inn Express Charleston by IHG

Holiday Inn Express Charleston by IHG

3.5 out of 5
West Ashley
Save 100% on your flight
Price was $799, price is now $531 per person
$531
per person
Oct 4 - Oct 10
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
Save 100% on your flight
Price was $2,051, price is now $1,219 per person
$1,219
per person
Oct 4 - Oct 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
The Beach Club at Charleston Harbor Resort and Marina

The Beach Club at Charleston Harbor Resort and Marina

4.5 out of 5
Save 100% on your flight
Price was $1,641, price is now $1,135 per person
$1,135
per person
Oct 4 - Oct 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
The Vendue

The Vendue

4 out of 5
Charleston Historic District
Save 100% on your flight
Price was $1,744, price is now $1,265 per person
$1,265
per person
Oct 4 - Oct 10
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, Sep 11 - Fri, Sep 11
BDL
Bradley Intl.
CHS
Charleston Intl.
$134 Roundtrip, found 20 hours ago
$134
Roundtrip
found 20 hours ago
Select Breeze Airways flight, departing Fri, Sep 11 from Bradley Intl. to Charleston Intl., returning Fri, Sep 11, priced at $134 found 20 hours ago
American Airlines
Tue, Oct 27 - Tue, Nov 3
DFW
Dallas-Fort Worth Intl.
CHS
Charleston Intl.
$197 Roundtrip, found 15 hours ago
$197
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Tue, Oct 27 from Dallas-Fort Worth Intl. to Charleston Intl., returning Tue, Nov 3, priced at $197 found 15 hours ago
Delta
Tue, Nov 3 - Tue, Nov 17
LGA
LaGuardia
CHS
Charleston Intl.
$199 Roundtrip, found 15 hours ago
$199
Roundtrip
found 15 hours ago
Select Delta flight, departing Tue, Nov 3 from LaGuardia to Charleston Intl., returning Tue, Nov 17, priced at $199 found 15 hours ago
Southwest Airlines
Sat, Oct 24 - Sat, Oct 31
DAL
Love Field
CHS
Charleston Intl.
$200 Roundtrip, just found
$200
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, Oct 24 from Love Field to Charleston Intl., returning Sat, Oct 31, priced at $200 just found