Callawassie Island Vacation Packages 2026 from $959

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The Latest Callawassie Island vacation packages

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

The Galloway House Inn

Midtown

Save 100% on your flight

$959

per person

Nov 10 - Nov 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Savannah (SAV)

9.6/10 Exceptional! (212 reviews)

Beautiful place,very clean and near to most attractions

Reviewed on Aug 20, 2026

Seawatch at Island Club

Mid Island

Save 100% on your flight

$1,149

per person

Oct 3 - Oct 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Savannah (SAV)

9.2/10 Wonderful! (49 reviews)

Kitchen was well stocked with cookware that was in like new condition. Beautiful, clean and cool. Good shower power. Great location for sunrise walks on the beach and short drive to everywhere. Friendly and welcome staff. Parking spots were quite narrow, though, so come with a compact car if possible! We will miss this island!

Reviewed on Aug 22, 2026

Hotel Bardo Savannah

Historic Downtown Savannah

Save 100% on your flight

$1,190

per person

Nov 6 - Nov 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Savannah (SAV)

9.4/10 Exceptional! (542 reviews)

My stay was amazing and I had a great room. The experience over all was relaxing

Reviewed on Aug 23, 2026

Foley House Inn

Historic Downtown Savannah

Save 100% on your flight

$1,196

per person

Oct 3 - Oct 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Savannah (SAV)

9.4/10 Exceptional! (519 reviews)

Charming historic property, huge room, amazing location, kind staff. Would stay again!

Reviewed on Aug 22, 2026

Godley Manor

Historic Downtown Savannah

Save 100% on your flight

$1,218

per person

Oct 3 - Oct 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Savannah (SAV)

9.8/10 Exceptional! (545 reviews)

Very charming and close to everything.

Reviewed on Aug 23, 2026

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What to do in Callawassie Island

90-Minute Savannah Riverboat Sightseeing Cruise

$42

per adult

90% of travellers recommend

Savannah Historical Guided Small Group Open-Air Minibus Tour

Savannah Historical Guided Open-Air Minibus Tour - Free Parking

$27

per adult

74% of travellers recommend

Savannah: Buffet Dinner Cruise with Live Entertainment

$93

per adult

90% of travellers recommend

See all activities in Callawassie Island

Callawassie Island Hotel Deals

Sonesta Resort Hilton Head Island

130 Shipyard Drive Hilton Head Island SC

Fully refundableReserve now, pay when you stay

$264 nightly

$290 total

Sep 1 - Sep 2

Total with taxes and fees

8.8/10 Excellent! (1,476 reviews)

"I loved Sonesta, friendly and clean."

Reviewed on Aug 24, 2026

Hilton Beachfront Resort & Spa Hilton Head Island

1 Hotel Circle Hilton Head Island SC

Fully refundableReserve now, pay when you stay

$250 nightly

$275 total

Aug 31 - Sep 1

Total with taxes and fees

8.4/10 Very Good! (1,601 reviews)

"The staff was outstanding! From the valet, to the front desk associates, to the bar and restaurant staff, they were all so very pleasant and helpful. We will definitely recommend the resort! The only critique I would offer, is that maybe the poolside bar stay open later."

Reviewed on Aug 23, 2026

The Westin Hilton Head Island Resort & Spa

2 Grasslawn Ave Hilton Head Island SC

Fully refundableReserve now, pay when you stay

$266 nightly

$292 total

Sep 23 - Sep 24

Total with taxes and fees

See all 10,959 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.