Vacations in Hilton Head Island

Vacations in Hilton Head Island

2 travelers

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Cheap Hilton Head Island package deals

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$531 - $977$977 - $1,424$1,424 - $1,870$1,870 - $2,316$2,316+ per night

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Most popular Hilton Head Island flight and hotel deals

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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
7.8 Good
Free Wi-Fi
Pool
Pet friendly
Boston Logan Intl
Meals not included
3 nights + flight
$578
Island Links Resort - Hilton Head Island
Island Links Resort - Hilton Head Island
Island Links Resort
Baltimore/Washington
Meals not included
3 nights + flight
$776
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
Boston Logan Intl
Breakfast
3 nights + flight
$607
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
Boston Logan Intl
Meals not included
3 nights + flight
$708
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
Boston Logan Intl
Meals not included
3 nights + flight
$744
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
Boston Logan Intl
Meals not included
3 nights + flight
$636
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
8.5 Very good
Free Wi-Fi
Pool
Pet friendly
Spa
Baltimore/Washington
Meals not included
3 nights + flight
$1,085
Hilton Garden Inn Hilton Head - Hilton Head Island - Restaurant
Hilton Garden Inn Hilton Head - Hilton Head Island - Restaurant
Hilton Garden Inn Hilton Head
8.2 Very good
Parking
Pool
Pet friendly
Boston Logan Intl
Meals not included
3 nights + flight
$656
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
Boston Logan Intl
Meals not included
3 nights + flight
$795
Xanadu A1 - Hilton Head Island - Pool
Xanadu A1 - Hilton Head Island - Pool
Xanadu A1
8.2 Very good
Parking
Free Wi-Fi
Pool
Boston Logan Intl
Meals not included
3 nights + flight
$914
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
8.7 Very good
Parking
Free Wi-Fi
Pool
Boston Logan Intl
Meals not included
3 nights + flight
$716
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
Boston Logan Intl
Breakfast
3 nights + flight
$607
Red Roof Inn Hilton Head Island - Hilton Head Island - Bedroom
Red Roof Inn Hilton Head Island - Hilton Head Island - Bedroom
Red Roof Inn Hilton Head Island
5.4 Fair
Parking
Free Wi-Fi
Pet friendly
Boston Logan Intl
Meals not included
3 nights + flight
$530
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
7.7 Good
Free Wi-Fi
Pool
Pet friendly
Baltimore/Washington
Breakfast
3 nights + flight
$696
Hotel Carolina - Hilton Head Island
Hotel Carolina - Hilton Head Island
Hotel Carolina
7 Good
Free Wi-Fi
Pool
New York John F Kennedy Intl
Meals not included
3 nights + flight
$674
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
New York John F Kennedy Intl
Meals not included
3 nights + flight
$867

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 $69; Family vacation $257; Romantic vacation $306; Luxury vacation $158; Budget vacation $144.

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)$69
Family vacation (Flight+Hotel)$257
Romantic vacation (Flight+Hotel)$306
Luxury vacation (Flight+Hotel)$158
Budget vacation (Flight+Hotel)$144