Vacations in Hilton Head Island

Vacations in Hilton Head Island

2 travellers
Fri 5/17
Mon 5/20

Search hundreds of travel sites at once for vacation package deals in Hilton Head Island

...and more

Let KAYAK do the searching

Save on your next vacation

Search and compare hundred of travel sites at once for vacation packages in Hilton Head Island, South Carolina

We’re completely free to use - No hidden charges or fees

Filter by free cancellation, free breakfast and more

Cheap Hilton Head Island package deals

Most popular Hilton Head Island flight and hotel deals

Show all
Spark by Hilton Hilton Head Island - Hilton Head Island - Restaurant
Spark by Hilton Hilton Head Island - Hilton Head Island - Restaurant
Spark by Hilton Hilton Head Island
7 Good
Free Wi-Fi
Pool
Pet friendly
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
C$ 480
Beach House Resort Hilton Head - Hilton Head Island - Pool
Beach House Resort Hilton Head - Hilton Head Island - Pool
Beach House Resort Hilton Head
7.9 Good
Pool
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 616
Hotel Carolina A Days Inn by Wyndham - Hilton Head Island - Building
Hotel Carolina A Days Inn by Wyndham - Hilton Head Island - Building
Hotel Carolina A Days Inn by Wyndham
5.3 Fair
Free Wi-Fi
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
C$ 350
The Westin Hilton Head Island Resort & Spa - Hilton Head Island - Outdoors view
The Westin Hilton Head Island Resort & Spa - Hilton Head Island - Outdoors view
The Westin Hilton Head Island Resort & Spa
8.3 Very good
Parking
Free Wi-Fi
Pool
Pet friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 1,132
Hilton Garden Inn Hilton Head - Hilton Head Island - Patio
Hilton Garden Inn Hilton Head - Hilton Head Island - Patio
Hilton Garden Inn Hilton Head
8.1 Very good
Parking
Free Wi-Fi
Pool
Pet friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 512
Sonesta Resort Hilton Head Island - Hilton Head Island - Lounge
Sonesta Resort Hilton Head Island - Hilton Head Island - Lounge
Sonesta Resort Hilton Head Island
7.8 Good
Pool
Pet friendly
Spa
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 821
Island Links Resort by Palmera - Hilton Head Island - Pool
Island Links Resort by Palmera - Hilton Head Island - Pool
Island Links Resort by Palmera
8.9 Very good
Parking
Free Wi-Fi
Pool
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 807
Hampton Inn Hilton Head - Hilton Head Island - Pool
Hampton Inn Hilton Head - Hilton Head Island - Pool
Hampton Inn Hilton Head
7.9 Good
Parking
Free Wi-Fi
Pool
Pet friendly
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
C$ 545
Grand Hilton Head Inn Ascend Hotel Collection - Hilton Head Island - Bedroom
Grand Hilton Head Inn Ascend Hotel Collection - Hilton Head Island - Bedroom
Grand Hilton Head Inn Ascend Hotel Collection
7.3 Good
Parking
Free Wi-Fi
Pool
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
C$ 530
SpringHill Suites by Marriott Hilton Head Island - Hilton Head Island - Restaurant
SpringHill Suites by Marriott Hilton Head Island - Hilton Head Island - Restaurant
SpringHill Suites by Marriott Hilton Head Island
8.2 Very good
Parking
Free Wi-Fi
Pool
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
C$ 486
Evian - Hilton Head Island - Dining room
Evian - Hilton Head Island - Dining room
Evian
8.3 Very good
Free Wi-Fi
Pool
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 761
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
5.7 Fair
Parking
Free Wi-Fi
Pool
Pet friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 335
Holiday Inn Express Hilton Head Island - Hilton Head Island - Bedroom
Holiday Inn Express Hilton Head Island - Hilton Head Island - Bedroom
Holiday Inn Express Hilton Head Island
6.9 Okay
Parking
Free Wi-Fi
Pool
Pet friendly
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
C$ 504
Omni Hilton Head Oceanfront Resort - Hilton Head Island - Pool
Omni Hilton Head Oceanfront Resort - Hilton Head Island - Pool
Omni Hilton Head Oceanfront Resort
8.5 Very good
Free Wi-Fi
Pool
Pet friendly
Spa
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 1,276
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
7.8 Good
Free Wi-Fi
Pool
New York LaGuardia
Meals not included
3 nights + flight
C$ 568
Hilton Head Resort 2107 - Hilton Head Island - Building
Hilton Head Resort 2107 - Hilton Head Island - Building
Hilton Head Resort 2107
8.2 Very good
Parking
Free Wi-Fi
Pool
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 1,048
Go to map

Search by stars

2+ stars3+ stars4+ stars5 stars

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by board

BreakfastHalf boardSelf cateringAll inclusiveMeals not included

Search by price

C$ 336 - C$ 1,120C$ 1,120 - C$ 1,904C$ 1,904 - C$ 2,689C$ 2,689 - C$ 3,473C$ 3,473+ per night

Search by freebies

Free breakfastFree internetFree airport shuttleFree parking

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.

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.