Search stays

3-night Kiawah Island vacations

Emeline

Emeline

4 out of 5
per person
Jun 3 - Jun 6
Roundtrip flight included
Chicago (CHI) to Charleston (CHS)
Elliott House Inn

Elliott House Inn

4 out of 5
per person
Jun 3 - Jun 6
Roundtrip flight included
Chicago (CHI) to Charleston (CHS)
The Francis Marion Hotel

The Francis Marion Hotel

4 out of 5
per person
Jun 3 - Jun 6
Roundtrip flight included
Chicago (CHI) to Charleston (CHS)
The Ryder Hotel

The Ryder Hotel

3.5 out of 5
per person
Jun 3 - Jun 6
Roundtrip flight included
Chicago (CHI) to Charleston (CHS)
Wingate By Wyndham Charleston

Wingate By Wyndham Charleston

2.5 out of 5
per person
Jun 3 - Jun 6
Roundtrip flight included
Chicago (CHI) to Charleston (CHS)
The Lindy Renaissance Charleston Hotel

The Lindy Renaissance Charleston Hotel

4 out of 5
per person
Jun 3 - Jun 6
Roundtrip flight included
Chicago (CHI) to Charleston (CHS)
Planters Inn

Planters Inn

4.5 out of 5
per person
Jun 3 - Jun 6
Roundtrip flight included
Chicago (CHI) to Charleston (CHS)
The Palmetto Hotel

The Palmetto Hotel

4 out of 5
per person
Jun 3 - Jun 6
Roundtrip flight included
Chicago (CHI) to Charleston (CHS)
The Loutrel

The Loutrel

4 out of 5
per person
Jun 3 - Jun 6
Roundtrip flight included
Chicago (CHI) to Charleston (CHS)
The Spectator Hotel

The Spectator Hotel

4 out of 5
per person
Jun 3 - Jun 6
Roundtrip flight included
Chicago (CHI) to Charleston (CHS)
French Quarter Inn

French Quarter Inn

4 out of 5
per person
Jun 3 - Jun 6
Roundtrip flight included
Chicago (CHI) to Charleston (CHS)
Andrew Pinckney Inn

Andrew Pinckney Inn

4 out of 5
per person
Jun 3 - Jun 6
Roundtrip flight included
Chicago (CHI) to Charleston (CHS)
Prices and availability subject to change. Additional terms may apply.

4-night Kiawah Island vacations

Hyatt House Charleston/Historic District

Hyatt House Charleston/Historic District

3 out of 5
Save 100% on your flight
per person
May 31 - Jun 4
Roundtrip non-stop flight included
Chicago (ORD) to Charleston (CHS)
Wingate By Wyndham Charleston

Wingate By Wyndham Charleston

2.5 out of 5
per person
May 31 - Jun 4
Roundtrip non-stop flight included
Chicago (ORD) to Charleston (CHS)
Elliott House Inn

Elliott House Inn

4 out of 5
Save 100% on your flight
per person
May 31 - Jun 4
Roundtrip non-stop flight included
Chicago (ORD) to Charleston (CHS)
Emeline

Emeline

4 out of 5
per person
Jun 6 - Jun 10
Roundtrip flight included
Grand Junction (GJT) to Charleston (CHS)
The Francis Marion Hotel

The Francis Marion Hotel

4 out of 5
per person
Jun 6 - Jun 10
Roundtrip flight included
Grand Junction (GJT) to Charleston (CHS)
Planters Inn

Planters Inn

4.5 out of 5
Save 100% on your flight
per person
May 31 - Jun 4
Roundtrip non-stop flight included
Chicago (ORD) to Charleston (CHS)
The Ryder Hotel

The Ryder Hotel

3.5 out of 5
per person
Jun 6 - Jun 10
Roundtrip flight included
Grand Junction (GJT) to Charleston (CHS)
The Spectator Hotel

The Spectator Hotel

4 out of 5
Save 100% on your flight
per person
May 31 - Jun 4
Roundtrip non-stop flight included
Chicago (ORD) to Charleston (CHS)
French Quarter Inn

French Quarter Inn

4 out of 5
Save 100% on your flight
per person
May 31 - Jun 4
Roundtrip non-stop flight included
Chicago (ORD) to Charleston (CHS)
Andrew Pinckney Inn

Andrew Pinckney Inn

4 out of 5
per person
May 31 - Jun 4
Roundtrip non-stop flight included
Chicago (ORD) to Charleston (CHS)
Indigo Inn

Indigo Inn

3 out of 5
per person
May 31 - Jun 4
Roundtrip flight included
Chicago (ORD) to Charleston (CHS)
Cambria Hotel Summerville - Charleston

Cambria Hotel Summerville - Charleston

3 out of 5
per person
May 31 - Jun 4
Roundtrip non-stop flight included
Chicago (ORD) to Charleston (CHS)
Prices and availability subject to change. Additional terms may apply.

5-night Kiawah Island vacations

Wingate By Wyndham Charleston

Wingate By Wyndham Charleston

2.5 out of 5
per person
May 26 - May 31
Roundtrip non-stop flight included
Chicago (ORD) to Charleston (CHS)
Emeline

Emeline

4 out of 5
Save 100% on your flight
per person
May 26 - May 31
Roundtrip non-stop flight included
Chicago (ORD) to Charleston (CHS)
Hyatt House Charleston/Historic District

Hyatt House Charleston/Historic District

3 out of 5
Save 100% on your flight
per person
May 26 - May 31
Roundtrip non-stop flight included
Chicago (ORD) to Charleston (CHS)
The Francis Marion Hotel

The Francis Marion Hotel

4 out of 5
Save 100% on your flight
per person
May 26 - May 31
Roundtrip non-stop flight included
Chicago (ORD) to Charleston (CHS)
The Ryder Hotel

The Ryder Hotel

3.5 out of 5
Save 100% on your flight
per person
May 26 - May 31
Roundtrip non-stop flight included
Chicago (ORD) to Charleston (CHS)
Elliott House Inn

Elliott House Inn

4 out of 5
Save 100% on your flight
per person
May 26 - May 31
Roundtrip non-stop flight included
Chicago (ORD) to Charleston (CHS)
Hyatt Place Charleston/Historic District

Hyatt Place Charleston/Historic District

3.5 out of 5
Save 100% on your flight
per person
May 26 - May 31
Roundtrip non-stop flight included
Chicago (ORD) to Charleston (CHS)
The Lindy Renaissance Charleston Hotel

The Lindy Renaissance Charleston Hotel

4 out of 5
Save 100% on your flight
per person
May 26 - May 31
Roundtrip non-stop flight included
Chicago (ORD) to Charleston (CHS)
Hotel Bennett

Hotel Bennett

5 out of 5
Save 100% on your flight
per person
May 26 - May 31
Roundtrip non-stop flight included
Chicago (ORD) to Charleston (CHS)
The Palmetto Hotel

The Palmetto Hotel

4 out of 5
Save 100% on your flight
per person
May 26 - May 31
Roundtrip non-stop flight included
Chicago (ORD) to Charleston (CHS)
The Restoration

The Restoration

4 out of 5
Save 100% on your flight
per person
May 26 - May 31
Roundtrip non-stop flight included
Chicago (ORD) to Charleston (CHS)
Indigo Inn

Indigo Inn

3 out of 5
Save 100% on your flight
per person
May 26 - May 31
Roundtrip non-stop flight included
Chicago (ORD) to Charleston (CHS)
Prices and availability subject to change. Additional terms may apply.

6-7 night Kiawah Island vacations

Tides Folly Beach Hotel

Tides Folly Beach Hotel

3 out of 5
per person
Jun 4 - Jun 10
Roundtrip non-stop flight included
Grand Junction (GJT) to Charleston (CHS)
Prices and availability subject to change. Additional terms may apply.

Flight deals to Kiawah Island

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

Tue, May 7 - Wed, May 8
EWR
Newark
CHS
Charleston
$41 Roundtrip, found 15 hours ago
$41
Roundtrip
found 15 hours ago
Select Spirit Airlines flight, departing Tue, May 7 from Newark to Charleston, returning Wed, May 8, priced at $41 found 15 hours ago
Sat, May 18 - Sat, May 18
PHL
Philadelphia
CHS
Charleston
$48 Roundtrip, found 2 days ago
$48
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, May 18 from Philadelphia to Charleston, returning Sat, May 18, priced at $48 found 2 days ago
Mon, May 13 - Fri, May 17
LGA
New York
CHS
Charleston
$65 Roundtrip, found 17 hours ago
$65
Roundtrip
found 17 hours ago
Select Spirit Airlines flight, departing Mon, May 13 from New York to Charleston, returning Fri, May 17, priced at $65 found 17 hours ago

Top rated hotels for your Kiawah Island vacation

The Sanctuary at Kiawah Island Golf Resort

The Sanctuary at Kiawah Island Golf Resort

5 out of 5
1 Sanctuary Beach Drive, Kiawah Island, SC
0.16 mi from city center
The price is $675 per night
$675
per night
Apr 21 - Apr 22
With a stay at The Sanctuary at Kiawah Island Golf Resort in Kiawah Island (East Beach), you'll be steps from Kiawah Island Beach and a 1-minute drive from Turtle Point Golf Course.
Charleston Kiawah Island/Andell Inn

Charleston Kiawah Island/Andell Inn

3.5 out of 5
300 Farm Lake View Road, Kiawah Island, SC
Free Cancellation
Reserve now, pay when you stay
3.18 mi from city center
The price is $329 per night
$329
per night
Apr 21 - Apr 22
Located in Kiawah Island, Charleston Kiawah Island/Andell Inn is next to a golf course, a 3-minute walk from Freshfields Village and 13 minutes by foot from Bohicket Marina.
Cottage w/ On-Site Golf, Shared Pool, & Beautiful Inlet Views - Near the Beach!

Cottage w/ On-Site Golf, Shared Pool, & Beautiful Inlet Views - Near the Beach!

2.2 mi from city center
Get rates
Located in Kiawah Island (West Beach), this cottage is within a 5-minute drive of Kiawah Beachwalker Park and Cougar Point Golf Course.
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.