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Vacations in Hilton Head Island

Vacations in Hilton Head Island

2 travellers

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C$ 628 - C$ 1,415C$ 1,415 - C$ 2,200C$ 2,200 - C$ 2,985C$ 2,985 - C$ 3,771C$ 3,771+ per night

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Most popular Hilton Head Island flight and hotel deals

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Courtyard by Marriott Hilton Head Island - Hilton Head Island - Patio
Courtyard by Marriott Hilton Head Island - Hilton Head Island - Patio
Courtyard by Marriott Hilton Head Island
8.6 Very good
Free Wi-Fi
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 835
Spark by Hilton Hilton Head Island - Hilton Head Island - Bedroom
Spark by Hilton Hilton Head Island - Hilton Head Island - Bedroom
Spark by Hilton Hilton Head Island
7.7 Good
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Breakfast
3 nights + flight
C$ 682
Island Links Resort - Hilton Head Island
Island Links Resort - Hilton Head Island
Island Links Resort
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 781
Palmera Inn and Suites - Hilton Head Island - Living room
Palmera Inn and Suites - Hilton Head Island - Living room
Palmera Inn and Suites
8.7 Very good
Parking
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Breakfast
3 nights + flight
C$ 702
Beach House Resort Hilton Head Island - Hilton Head Island - Bar
Beach House Resort Hilton Head Island - Hilton Head Island - Bar
Beach House Resort Hilton Head Island
7.8 Good
Pool
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 768
Hilton Beachfront Resort and Spa Hilton Head Island - Hilton Head Island - Pool
Hilton Beachfront Resort and Spa Hilton Head Island - Hilton Head Island - Pool
Hilton Beachfront Resort and Spa Hilton Head Island
7.8 Good
Free Wi-Fi
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 826
DoubleTree by Hilton Hilton Head Island - Hilton Head Island - Bedroom
DoubleTree by Hilton Hilton Head Island - Hilton Head Island - Bedroom
DoubleTree by Hilton Hilton Head Island
7.9 Good
Parking
Free Wi-Fi
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 767
The Westin Hilton Head Island Resort & Spa - Hilton Head Island - Building
The Westin Hilton Head Island Resort & Spa - Hilton Head Island - Building
The Westin Hilton Head Island Resort & Spa
8.4 Very good
Free Wi-Fi
Pool
Pet friendly
Spa
San Juan Luis Munoz Marin Intl
Meals not included
3 nights + flight
C$ 1,508
477 Plantation Club Villas at The Sea Pines Resort - Hilton Head Island - Beach
477 Plantation Club Villas at The Sea Pines Resort - Hilton Head Island - Beach
477 Plantation Club Villas at The Sea Pines Resort
Free Wi-Fi
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 1,511
Sonesta Resort Hilton Head Island - Hilton Head Island - Pool
Sonesta Resort Hilton Head Island - Hilton Head Island - Pool
Sonesta Resort Hilton Head Island
8.5 Very good
Pool
Pet friendly
Spa
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 907
Xanadu A1 - Hilton Head Island - Pool
Xanadu A1 - Hilton Head Island - Pool
Xanadu A1
8.2 Very good
Parking
Free Wi-Fi
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 1,177
Coral Sands Resorts by Palmera - Hilton Head Island - Living room
Coral Sands Resorts by Palmera - Hilton Head Island - Living room
Coral Sands Resorts by Palmera
8.6 Very good
Parking
Free Wi-Fi
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 794
Hampton Inn Hilton Head - Hilton Head Island - Pool
Hampton Inn Hilton Head - Hilton Head Island - Pool
Hampton Inn Hilton Head
8.2 Very good
Parking
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Breakfast
3 nights + flight
C$ 875
Marriott's Grande Ocean, A Marriott Vacation Club Resort - Hilton Head Island
Marriott's Grande Ocean, A Marriott Vacation Club Resort - Hilton Head Island
Marriott's Grande Ocean, A Marriott Vacation Club Resort
8.9 Very good
Free Wi-Fi
Pool
Spa
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 1,620
Fiddler's Cove 4S - Hilton Head Island
Fiddler's Cove 4S - Hilton Head Island
Fiddler's Cove 4S
5.7 Fair
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 931
Holiday Inn Express Hilton Head Island By IHG - Hilton Head Island - Bedroom
Holiday Inn Express Hilton Head Island By IHG - Hilton Head Island - Bedroom
Holiday Inn Express Hilton Head Island By IHG
7.6 Good
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Breakfast
3 nights + flight
C$ 690

When to book a vacation in Hilton Head Island

Price includes flights and 3 nights accommodation for 2 travellers. Prices are not fixed and may vary with time.

Tips for finding Hilton Head Island package deals

  • There are loads of types of vacations in Hilton Head Island and the cost will depend on what type of trip you’re taking and for how long you’d like to stay. Here are the latest prices for a 3 night trip for 2 travellers: Top vacation C$ 389; Family vacation C$ 601; Romantic vacation C$ 1,051.

Where to stay in Hilton Head Island

Our map will help you find the perfect place to stay for your vacation in Hilton Head Island by showing you the exact location of each hotel.

Everything you need to know for your vacation in Hilton Head Island

Hilton Head Island vacation information

Top vacation (Flight+Hotel)C$ 389
Family vacation (Flight+Hotel)C$ 601
Romantic vacation (Flight+Hotel)C$ 1,051