Callawassie Island Vacation Packages 2025/2026 from $371

Callawassie Island flight + hotel vacation packages

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

Iris Garden Inn

$371

per person

Dec 7 - Dec 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Savannah (SAV)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the business center and free internet in public areas. There's a gym on site, and a terrace and a garden are also provided.

Sonesta Resort Hilton Head Island

South End

Save 100% on your flight

$520

per person

Jan 20 - Jan 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Savannah (SAV)

A full-service spa, 5 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Families will appreciate the children's club and onsite laundry facilities. Unwind with a drink at one of the 3 bars/lounges and enjoy perks like a free area shuttle.

The Westin Hilton Head Island Resort & Spa

Mid Island

Save 100% on your flight

$669

per person

Jan 20 - Jan 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Savannah (SAV)

This smoke-free hotel features a golf course, a full-service spa, and 2 restaurants. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area.

Staybridge Suites Savannah Historic District by IHG

Historic Downtown Savannah

$374

per person

Jan 15 - Jan 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Savannah (SAV)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. Self parking, a 24-hour business center, and a grocery/convenience store are also offered.

Top Callawassie Island hotels deals

Hilton Beachfront Resort & Spa Hilton Head Island

1 Hotel Circle, Hilton Head Island, SC

Free Cancellation

Reserve now, pay when you stay

$182 nightly

$200 total

Nov 12 - Nov 13

Total with taxes and fees

A full-service spa, 5 restaurants, and 2 outdoor pools are all featured at this luxury resort. Dine at the beachfront restaurant and relax with beach umbrellas. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

Holiday Inn Express Hilton Head Island by IHG

10 Tanglewood Drive, Hilton Head Island, SC

Free Cancellation

$93 nightly

$102 total

Nov 30 - Dec 1

Total with taxes and fees

This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy freebies like buffet breakfast and a beach shuttle

Sonesta Resort Hilton Head Island

130 Shipyard Drive, Hilton Head Island, SC

Free Cancellation

Reserve now, pay when you stay

$232 nightly

$255 total

Nov 23 - Nov 24

Total with taxes and fees

Omni Hilton Head Oceanfront Resort

23 Ocean Lane, Hilton Head Island, SC

Free Cancellation

Reserve now, pay when you stay

$238 nightly

$257 total

Nov 30 - Dec 1

Total with taxes and fees

A full-service spa, 3 restaurants, and 3 outdoor pools are all featured at this smoke-free resort. There's fun for all ages with a children's club and a children's pool, and supervised childcare is an added bonus. Relax with a drink at one of the 2 poolside bars and enjoy free perks like free self parking and WiFi in public areas.

Pool

Spa

Beach House Resort Hilton Head

1 South Forest Beach Drive, Hilton Head Island, SC

Free Cancellation

Reserve now, pay when you stay

$164 nightly

$180 total

Dec 2 - Dec 3

Total with taxes and fees

This hotel features 2 bars/lounges, a beach bar, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. You'll appreciate the outdoor pool, poolside bar, and concierge services.

Pool

Pet friendly

The Westin Hilton Head Island Resort & Spa

2 Grasslawn Ave, Hilton Head Island, SC

Free Cancellation

Reserve now, pay when you stay

$185 nightly

$204 total

Nov 23 - Nov 24

Total with taxes and fees

Pool

Hot Tub

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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.

Popular places to visit

Tanger Outlets Hilton Head

You can search for that perfect souvenir at Tanger Outlets Hilton Head during your trip to Bluffton. Wander the beautiful beaches and seaside in this family-friendly area.

May River Golf Club at Palmetto Bluff

Enjoy a round of golf in Bluffton at May River Golf Club at Palmetto Bluff. Wander the beautiful beaches and seaside in this family-friendly area.

Rose Hill Mansion

You can find out about the history of Bluffton with a stop at Rose Hill Mansion. Amble around this family-friendly area's beautiful beaches, or seek out the golf courses.

Frequently asked questions

How much are vacation packages to Callawassie Island?

Travelocity has package deals to Callawassie Island, as well as flights and hotels, starting from as low as $371. With all the extra cash, you could purchase some cool tours or maybe also add a couple of extra nights to your adventure.

Where can I get the best vacation package deals for Callawassie Island?

You'll discover a terrific range of Callawassie Island package deals on Travelocity. With no less than 400 partner airlines and 1,000,000 properties across the globe, organizing the ultimate vacation will be simple.

Why should I book my Callawassie Island vacation bundle via Travelocity?

We have experiences and destinations to suit every type of traveler, exceptional service and round-the-clock customer support. And to top it off, we'll match any better price you're able to find with our Price Match Guarantee.

Will I save money on my Callawassie Island car rental if I book it with hotels and flights?

Combining your bookings into a Callawassie Island vacation package will leave you with some serious savings. Combine a car and flight; a hotel, car and flight; or a car and hotel. You won't find a better way to explore the greater Callawassie Island region than with your own ride. You can also add tours and experiences to your Travelocity package.

Where should I stay when visiting Callawassie Island?

If you're looking for someplace comfortable to base yourself, check out the Bright 3 Bdrm -2 bath Coastal Villa on Exclusive Callawassi Island-Golf Included. It's the top choice for many travelers.