Vacations in Hilton Head Island

Vacations in Hilton Head Island

2 travelers

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Cheap Hilton Head Island package deals

These are the best prices for Jun 9 - 12.
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$419 - $1,162$1,162 - $1,905$1,905 - $2,649$2,649 - $3,392$3,392+ 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
8.5 Very good
Free Wi-Fi
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
$726
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
7.9 Good
Parking
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Breakfast
3 nights + flight
$524
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
$523
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
8 Very good
Pool
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$764
Hilton Beachfront Resort and Spa Hilton Head Island - Hilton Head Island - Lounge
Hilton Beachfront Resort and Spa Hilton Head Island - Hilton Head Island - Lounge
Hilton Beachfront Resort and Spa Hilton Head Island
8 Very good
Free Wi-Fi
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
$781
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
7.8 Good
Parking
Free Wi-Fi
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
$694
The Westin Hilton Head Island Resort & Spa - Hilton Head Island - Restaurant
The Westin Hilton Head Island Resort & Spa - Hilton Head Island - Restaurant
The Westin Hilton Head Island Resort & Spa
8.5 Very good
Free Wi-Fi
Pool
Pet friendly
Spa
Chicago O'Hare Intl
Meals not included
3 nights + flight
$844
Home2 Suites by Hilton Hilton Head - Hilton Head Island - Patio
Home2 Suites by Hilton Hilton Head - Hilton Head Island - Patio
Home2 Suites by Hilton Hilton Head
8.6 Very good
Parking
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Breakfast
3 nights + flight
$675
Hilton Garden Inn Hilton Head - Hilton Head Island - Restaurant
Hilton Garden Inn Hilton Head - Hilton Head Island - Restaurant
Hilton Garden Inn Hilton Head
8.3 Very good
Parking
Pool
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$529
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
$815
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
$487
SpringHill Suites by Marriott Hilton Head Island - Hilton Head Island - Building
SpringHill Suites by Marriott Hilton Head Island - Hilton Head Island - Building
SpringHill Suites by Marriott Hilton Head Island
8.5 Very good
Parking
Free Wi-Fi
Pool
Chicago O'Hare Intl
Breakfast
3 nights + flight
$576
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
7.8 Good
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Breakfast
3 nights + flight
$534
Omni Hilton Head Oceanfront Resort - Hilton Head Island - Pool
Omni Hilton Head Oceanfront Resort - Hilton Head Island - Pool
Omni Hilton Head Oceanfront Resort
8.6 Very good
Pool
Pet friendly
Spa
Chicago O'Hare Intl
Meals not included
3 nights + flight
$1,035
Hotel Carolina - Hilton Head Island - Building
Hotel Carolina - Hilton Head Island - Building
Hotel Carolina
6.5 Okay
Parking
Free Wi-Fi
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
$472
Hilton Head Island Beach & Tennis Resort - Hilton Head Island - Pool
Hilton Head Island Beach & Tennis Resort - Hilton Head Island - Pool
Hilton Head Island Beach & Tennis Resort
7.7 Good
Free Wi-Fi
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
$692

Last minute vacation packages to Hilton Head Island

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Marriott's Barony Beach Club - Hilton Head Island - Pool
Marriott's Barony Beach Club - Hilton Head Island - Pool
Marriott's Barony Beach Club
Free Wi-Fi
Pool
Spa
Salt Lake City
Meals not included
3 nights + flight
$2,411
Marriott's Monarch at Sea Pines, A Marriott Vacation Club Resort - Hilton Head Island - Pool
Marriott's Monarch at Sea Pines, A Marriott Vacation Club Resort - Hilton Head Island - Pool
Marriott's Monarch at Sea Pines, A Marriott Vacation Club Resort
8.3 Very good
Free Wi-Fi
Pool
Salt Lake City
Meals not included
3 nights + flight
$1,966
530 Plantation Club Villas at The Sea Pines Resort - Hilton Head Island - Beach
530 Plantation Club Villas at The Sea Pines Resort - Hilton Head Island - Beach
530 Plantation Club Villas at The Sea Pines Resort
Parking
Free Wi-Fi
Pool
Salt Lake City
Meals not included
3 nights + flight
$1,527

When to book a vacation in Hilton Head Island

Price includes flights and 3 nights accommodation for 2 travelers. 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 travelers: Top vacation $68; Family vacation $249; Romantic vacation $306; Luxury vacation $158; Budget vacation $218.

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)$68
Family vacation (Flight+Hotel)$249
Romantic vacation (Flight+Hotel)$306
Luxury vacation (Flight+Hotel)$158
Budget vacation (Flight+Hotel)$218