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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.
The Ryder Hotel

The Ryder Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,627, price is now $975 per person
$975
per person
Oct 12 - Oct 17
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 Port of Charleston are located nearby.

Planters Inn

Planters Inn

4.5 out of 5
Save 100% on your flight
Price was $2,970, price is now $2,165 per person
$2,165
per person
Oct 6 - Oct 13
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 clean rooms in our reviews. Popular attractions Charleston City Market and Port of Charleston are located nearby.
Love it! The staff here were a 10/10. They were super helpful and extremely nice. I landed very early and asked for early check in due to being up since 1am that day. They had the staff prepare a room in under an hour. I can’t thank them enough for that. Rooms were clean. Property was really pretty. It was extremely close to all the shopping/things to do. My only complaint is the charge for valet parking. It was 40 dollars each time you used it and no one communicated that to us. At the end of the stay I had a 240 dollar charge that I wasn’t expecting. But everything else was a 10/10

Reviewed on Jul 28, 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 $3,199, price is now $2,336 per person
$2,336
per person
Oct 12 - Oct 17
found 12 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 Isle of Palms Beach and Front Beach are located nearby.

1111 Middle Street by Avantstay Charming Historic Cottage Featured in "dear John" Movie Beach Access

1111 Middle Street by Avantstay Charming Historic Cottage Featured in "dear John" Movie Beach Access

3 out of 5
Save 100% on your flight
Price was $3,338, price is now $2,443 per person
$2,443
per person
Oct 12 - Oct 17
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
Book a stay at this beach cottage in Sullivan's Island. Enjoy free parking, a beach locale, and balconies. Popular attractions Isle of Palms Beach and Sullivan's Island Beach are located nearby.

Lighthouse by Avantstay Beachfront View Home w/ Pool Table & Ping Pong

Lighthouse by Avantstay Beachfront View Home w/ Pool Table & Ping Pong

3.5 out of 5
Save 100% on your flight
Price was $9,837, price is now $7,267 per person
$7,267
per person
Oct 6 - Oct 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
Book a stay at this beach cottage in Folly Beach. Enjoy free parking, a beach locale, and concierge services. Popular attractions Folly Island Beaches and Folly River Park are located nearby.

Emeline

Emeline

4 out of 5
Price was $1,663, price is now $1,230 per person
$1,230
per person
Sep 3 - Sep 7
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 Port of Charleston are located nearby.

Haven by Avantstay Luxury Beachfront Home w/ Pool & Gorgeous Patios

Haven by Avantstay Luxury Beachfront Home w/ Pool & Gorgeous Patios

3.5 out of 5
Save 100% on your flight
Price was $8,619, price is now $6,379 per person
$6,379
per person
Oct 6 - Oct 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
Book a stay at this beach vacation home in Sullivan's Island. Enjoy free parking, a beach locale, and concierge services. Popular attractions Isle of Palms Beach and Sullivan's Island Beach are located nearby.

5 32nd Avenue by Avantstay Gourmet Kitchen Pool Balconies

5 32nd Avenue by Avantstay Gourmet Kitchen Pool Balconies

3 out of 5
Save 100% on your flight
Price was $3,232, price is now $2,434 per person
$2,434
per person
Oct 12 - Oct 17
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
Stay at this cottage in Isle of Palms. Enjoy free parking, balconies, and in-room washers/dryers. Popular attractions Isle of Palms Beach and Front Beach are located nearby.

Kiawah Island Vacation Packages 3-4 Night Stays

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

The Francis Marion Hotel

4 out of 5
Charleston Historic District
Save 100% on your flight
Price was $831, price is now $616 per person
$616
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Charleston (CHS)
The Ryder Hotel

The Ryder Hotel

3.5 out of 5
Charleston Historic District
Save 100% on your flight
Price was $1,346, price is now $917 per person
$917
per person
Oct 16 - Oct 19
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Charleston (CHS)
Planters Inn

Planters Inn

4.5 out of 5
Charleston Historic District
Save 100% on your flight
Price was $1,484, price is now $1,071 per person
$1,071
per person
Oct 14 - Oct 17
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
Emeline

Emeline

4 out of 5
Charleston Historic District
Price was $1,663, price is now $1,230 per person
$1,230
per person
Sep 3 - Sep 7
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.
The Francis Marion Hotel

The Francis Marion Hotel

4 out of 5
Charleston Historic District
Save 100% on your flight
Price was $1,040, price is now $736 per person
$736
per person
Aug 31 - Sep 5
found 2 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Charleston (CHS)
The Ryder Hotel

The Ryder Hotel

3.5 out of 5
Charleston Historic District
Save 100% on your flight
Price was $1,627, price is now $975 per person
$975
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charleston (CHS)
Planters Inn

Planters Inn

4.5 out of 5
Charleston Historic District
Save 100% on your flight
Price was $2,970, price is now $2,165 per person
$2,165
per person
Oct 6 - Oct 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
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 $3,199, price is now $2,336 per person
$2,336
per person
Oct 12 - Oct 17
found 12 hours 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.
$98 Roundtrip, just found
$98
Roundtrip
just found
Select Breeze Airways flight, departing Fri, Sep 11 from Bradley Intl. to Charleston Intl., returning Fri, Sep 11, priced at $98 just found
Bargain Flight
Wed, Aug 19 - Tue, Aug 25
DCA
Ronald Reagan Washington National
CHS
Charleston Intl.
$187 Roundtrip, found 2 days ago
$187
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Wed, Aug 19 from Ronald Reagan Washington National to Charleston Intl., returning Tue, Aug 25, priced at $187 found 2 days ago
Breeze Airways
Thu, Oct 1 - Sun, Oct 4
TTN
Mercer
CHS
Charleston Intl.
$189 Roundtrip, found 3 days ago
$189
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Oct 1 from Mercer to Charleston Intl., returning Sun, Oct 4, priced at $189 found 3 days ago
Breeze Airways
Mon, Sep 7 - Fri, Sep 11
SWF
Stewart Intl.
CHS
Charleston Intl.
$200 Roundtrip, found 3 days ago
$200
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Mon, Sep 7 from Stewart Intl. to Charleston Intl., returning Fri, Sep 11, priced at $200 found 3 days ago