Callawassie Island Vacation Packages 2026 from $1,148

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The Latest Callawassie Island vacation packages

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

JW Marriott Savannah Plant Riverside District

Historic Downtown Savannah

Save 100% on your flight

$1,148

per person

Nov 5 - Nov 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Savannah (SAV)

9.4/10 Exceptional! (1,566 reviews)

Olde Harbour Inn

Historic Downtown Savannah

Save 100% on your flight

$1,213

per person

Dec 20 - Dec 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Savannah (SAV)

9.6/10 Exceptional! (1,006 reviews)

Great location and nice place to stay with a pet. We love the spacious accommodations.

Reviewed on Oct 2, 2026

Seawatch at Island Club

Mid Island

Save 100% on your flight

$1,406

per person

Dec 20 - Dec 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Savannah (SAV)

9.4/10 Exceptional! (55 reviews)

The room was spotless, clean and appeared to be recently upgraded. The access to the beach was great and the storage box full of beach toys for children that previous vacationers left for others to enjoy was a wonderful idea.

Reviewed on Sep 13, 2026

Thompson Savannah, by Hyatt

Hitch Village - Fred Wessels Homes

Save 100% on your flight

$1,208

per person

Nov 5 - Nov 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Savannah (SAV)

9.4/10 Exceptional! (1,003 reviews)

Sweetbay by Avantstay 1 Min Walk to Beach + Pool

Mid Island

Save 100% on your flight

$3,722

per person

Dec 20 - Dec 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Savannah (SAV)

No reviews

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What to do in Callawassie Island

90-Minute Savannah Riverboat Sightseeing Cruise

$42

per adult

90% of travellers recommend

Savannah: Buffet Dinner Cruise with Live Entertainment

$93

per adult

90% of travellers recommend

Savannah Historical Guided Open-Air Minibus Cruiser- Free Parking

$30

per adult

80% of travellers recommend

See all activities in Callawassie Island

Callawassie Island Hotel Deals

Hilton Beachfront Resort & Spa Hilton Head Island

1 Hotel Circle Hilton Head Island SC

Fully refundableReserve now, pay when you stay

$209 nightly

$230 total

Oct 30 - Oct 31

Total with taxes and fees

8.4/10 Very Good! (1,654 reviews)

"We loved our stay at this property and the Hilton Head area. So convenient to everything and walkable and bikeable. Lovely property. Would stay here again."

Reviewed on Oct 3, 2026

Holiday Inn Express Hilton Head Island by IHG

10 Tanglewood Drive Hilton Head Island SC

Fully refundable

$119 nightly

$131 total

Nov 2 - Nov 3

Total with taxes and fees

8.4/10 Very Good! (819 reviews)

"I usually stay at the Sleep Inn when I travel next, this time I made reservations with the Holiday Inn Express and was very impressed.. The breakfast the next morning was excellent. When I come back I will stay there again.."

Reviewed on Oct 3, 2026

Palmera Inn and Suites

12 Park Ln Hilton Head Island SC

Fully refundableReserve now, pay when you stay

$112 nightly

$121 total

Nov 1 - Nov 2

Total with taxes and fees

See all 10,890 properties in Callawassie Island

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.