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3-night Harbor Island vacations

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

Thunderbird Inn

2 out of 5
per person
Jun 9 - Jun 12
Roundtrip non-stop flight included
Chicago (CHI) to Savannah (SAV)
The Galloway House Inn

The Galloway House Inn

4 out of 5
per person
Jun 9 - Jun 12
Roundtrip non-stop flight included
Chicago (CHI) to Savannah (SAV)
Godley Manor

Godley Manor

3 out of 5
per person
Jun 9 - Jun 12
Roundtrip non-stop flight included
Chicago (CHI) to Savannah (SAV)
Staybridge Suites Savannah Historic District, an IHG Hotel

Staybridge Suites Savannah Historic District, an IHG Hotel

3 out of 5
per person
Jun 9 - Jun 12
Roundtrip non-stop flight included
Chicago (CHI) to Savannah (SAV)
Hotel Tybee

Hotel Tybee

2.5 out of 5
per person
Jun 9 - Jun 12
Roundtrip non-stop flight included
Chicago (CHI) to Savannah (SAV)
Spark By Hilton Hilton Head Island

Spark By Hilton Hilton Head Island

2.5 out of 5
per person
Jun 9 - Jun 12
Roundtrip non-stop flight included
Chicago (CHI) to Savannah (SAV)
Hampton Inn Savannah-Historic District

Hampton Inn Savannah-Historic District

2.5 out of 5
per person
Jun 9 - Jun 12
Roundtrip non-stop flight included
Chicago (CHI) to Savannah (SAV)
DeSoto Beach Hotel

DeSoto Beach Hotel

3 out of 5
per person
Jun 9 - Jun 12
Roundtrip non-stop flight included
Chicago (CHI) to Savannah (SAV)
Azalea Inn and Villas

Azalea Inn and Villas

4.5 out of 5
per person
Jun 9 - Jun 12
Roundtrip non-stop flight included
Chicago (CHI) to Savannah (SAV)
17Hundred90 Inn and Restaurant

17Hundred90 Inn and Restaurant

3 out of 5
per person
Jun 9 - Jun 12
Roundtrip non-stop flight included
Chicago (CHI) to Savannah (SAV)
Sonder The Broughton

Sonder The Broughton

4 out of 5
per person
Jun 9 - Jun 12
Roundtrip non-stop flight included
Chicago (CHI) to Savannah (SAV)
Olde Harbour Inn

Olde Harbour Inn

4 out of 5
per person
Jun 9 - Jun 12
Roundtrip non-stop flight included
Chicago (CHI) to Savannah (SAV)

4-night Harbor Island vacations

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

Elliott House Inn

4 out of 5
Save 100% on your flight
per person
Jun 20 - Jun 24
Roundtrip flight included
Chicago (ORD) to Charleston (CHS)
Sonesta Resort Hilton Head Island

Sonesta Resort Hilton Head Island

4 out of 5
per person
Jun 24 - Jun 28
Roundtrip flight included
Chicago (ORD) to Savannah (SAV)
Palmera Inn and Suites

Palmera Inn and Suites

3 out of 5
per person
Jun 24 - Jun 28
Roundtrip flight included
Chicago (ORD) to Savannah (SAV)
Wingate By Wyndham Charleston

Wingate By Wyndham Charleston

2.5 out of 5
per person
Jun 20 - Jun 24
Roundtrip flight included
Chicago (ORD) to Charleston (CHS)
The Ryder Hotel

The Ryder Hotel

3.5 out of 5
per person
Jun 20 - Jun 24
Roundtrip flight included
Chicago (ORD) to Charleston (CHS)
Hilton Club Liberty Place Charleston

Hilton Club Liberty Place Charleston

3.5 out of 5
per person
Jun 20 - Jun 24
Roundtrip flight included
Chicago (ORD) to Charleston (CHS)
Sandcastle Inn

Sandcastle Inn

2.5 out of 5
per person
Jun 5 - Jun 9
Roundtrip flight included
Chicago (ORD) to Savannah (SAV)
Planters Inn

Planters Inn

4.5 out of 5
per person
Jun 20 - Jun 24
Roundtrip flight included
Chicago (ORD) to Charleston (CHS)
The Spectator Hotel

The Spectator Hotel

4 out of 5
per person
Jun 20 - Jun 24
Roundtrip flight included
Chicago (ORD) to Charleston (CHS)
French Quarter Inn

French Quarter Inn

4 out of 5
per person
Jun 20 - Jun 24
Roundtrip flight included
Chicago (ORD) to Charleston (CHS)
The Loutrel

The Loutrel

4 out of 5
per person
Jun 20 - Jun 24
Roundtrip flight included
Chicago (ORD) to Charleston (CHS)
Harborside at Charleston Harbor Resort and Marina

Harborside at Charleston Harbor Resort and Marina

4 out of 5
per person
Jun 20 - Jun 24
Roundtrip flight included
Chicago (ORD) to Charleston (CHS)

6-7 night Harbor Island vacations

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

Elliott House Inn

4 out of 5
Save 100% on your flight
per person
Jun 15 - Jun 22
Roundtrip non-stop flight included
Chicago (ORD) to Charleston (CHS)
Emeline

Emeline

4 out of 5
Save 100% on your flight
per person
Jun 15 - Jun 22
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
Jun 15 - Jun 22
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
Jun 15 - Jun 22
Roundtrip non-stop flight included
Chicago (ORD) to Charleston (CHS)
The Inn At Middleton Place

The Inn At Middleton Place

3 out of 5
per person
Jun 15 - Jun 22
Roundtrip non-stop flight included
Chicago (ORD) to Charleston (CHS)
Hilton Club Liberty Place Charleston

Hilton Club Liberty Place Charleston

3.5 out of 5
Save 100% on your flight
per person
Jun 15 - Jun 22
Roundtrip non-stop flight included
Chicago (ORD) to Charleston (CHS)
Planters Inn

Planters Inn

4.5 out of 5
Save 100% on your flight
per person
Jun 15 - Jun 22
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
Jun 15 - Jun 22
Roundtrip non-stop flight included
Chicago (ORD) to Charleston (CHS)
The Spectator Hotel

The Spectator Hotel

4 out of 5
Save 100% on your flight
per person
Jun 15 - Jun 22
Roundtrip non-stop flight included
Chicago (ORD) to Charleston (CHS)
The Loutrel

The Loutrel

4 out of 5
Save 100% on your flight
per person
Jun 15 - Jun 22
Roundtrip non-stop flight included
Chicago (ORD) to Charleston (CHS)
Andrew Pinckney Inn

Andrew Pinckney Inn

4 out of 5
per person
Jun 15 - Jun 22
Roundtrip non-stop flight included
Chicago (ORD) to Charleston (CHS)
Harborside at Charleston Harbor Resort and Marina

Harborside at Charleston Harbor Resort and Marina

4 out of 5
per person
Jun 15 - Jun 22
Roundtrip non-stop flight included
Chicago (ORD) to Charleston (CHS)

Flight deals to Harbor Island

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

Sat, May 18 - Tue, May 21
LGA
New York
CHS
Charleston
$41 Roundtrip, found 4 days ago
$41
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Sat, May 18 from New York to Charleston, returning Tue, May 21, priced at $41 found 4 days ago
Wed, May 29 - Wed, Jun 5
EWR
Newark
CHS
Charleston
$51 Roundtrip, found 6 days ago
$51
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Wed, May 29 from Newark to Charleston, returning Wed, Jun 5, priced at $51 found 6 days ago
Sat, May 11 - Wed, May 15
PHL
Philadelphia
CHS
Charleston
$58 Roundtrip, found 3 hours ago
$58
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, May 11 from Philadelphia to Charleston, returning Wed, May 15, priced at $58 found 3 hours ago

Top rated hotels for your Harbor Island vacation

Gorgeous Ocean View. Stylish, Clean & Pet Friendly Hunting Island Pass Included!

Gorgeous Ocean View. Stylish, Clean & Pet Friendly Hunting Island Pass Included!

1.31 mi from city center
The price is $164 per night
$164
per night
May 1 - May 2
Located in Saint Helena Island, this condo is by the ocean, within a 15-minute drive of Hunting Island Lighthouse and Ocean Point Golf Course.
Oceanview 4BR/3BA, Pet Friendly in Pelican Point

Oceanview 4BR/3BA, Pet Friendly in Pelican Point

1.25 mi from city center
Get rates
Located in Saint Helena Island, this vacation home is by the ocean, within a 15-minute drive of Hunting Island Lighthouse and Ocean Point Golf Course.
Pool
Pet friendly
The Westin Hilton Head Island Resort & Spa

The Westin Hilton Head Island Resort & Spa

4 out of 5
2 Grasslawn Ave, Hilton Head Island, SC
Free Cancellation
Reserve now, pay when you stay
18.63 mi from city center
The price is $349 per night
$349
per night
May 12 - May 13
Located in Hilton Head Island, The Westin Hilton Head Island Resort & Spa is by the ocean, within a 10-minute drive of Coastal Discovery Museum and Shelter Cove Harbour.
Pool
Pet friendly
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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.