Search
Best Deals
Vacations in Hilton Head Island

Vacations in Hilton Head Island

2 travellers

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

Here is why travelers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap Hilton Head Island package deals

Discover the best prices and deals for you by selecting your travel dates.
Choose your dates

Most popular Hilton Head Island flight and hotel deals

Show all
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
8.9 Very good
Parking
Free Wi-Fi
Pool
Hartford Bradley Intl
Meals not included
3 nights + flight
C$ 607
Spark by Hilton Hilton Head Island - Hilton Head Island - Dining room
Spark by Hilton Hilton Head Island - Hilton Head Island - Dining room
Spark by Hilton Hilton Head Island
7.3 Good
Free Wi-Fi
Pool
Pet friendly
Hartford Bradley Intl
Breakfast
3 nights + flight
C$ 455
Beach House Resort Hilton Head - Hilton Head Island - Restaurant
Beach House Resort Hilton Head - Hilton Head Island - Restaurant
Beach House Resort Hilton Head
7.9 Good
Pool
New York LaGuardia
Meals not included
3 nights + flight
C$ 661
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
New York LaGuardia
Breakfast
3 nights + flight
C$ 590
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
New York LaGuardia
Meals not included
3 nights + flight
C$ 738
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
6.2 Okay
Parking
Free Wi-Fi
Pool
New York LaGuardia
Breakfast
3 nights + flight
C$ 399
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
8.4 Very good
Parking
Free Wi-Fi
Pool
Pet friendly
Minneapolis St Paul
Meals not included
3 nights + flight
C$ 735
The Spa 1219 - Hilton Head Island - Living room
The Spa 1219 - Hilton Head Island - Living room
The Spa 1219
Parking
Free Wi-Fi
Pool
New York LaGuardia
Meals not included
3 nights + flight
C$ 731
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
8.5 Very good
Parking
Free Wi-Fi
Pool
Pet friendly
Hartford Bradley Intl
Breakfast
3 nights + flight
C$ 521
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
Hartford Bradley Intl
Meals not included
3 nights + flight
C$ 480
Waterside by Spinnaker Resorts - Hilton Head Island - Outdoors view
Waterside by Spinnaker Resorts - Hilton Head Island - Outdoors view
Waterside by Spinnaker Resorts
8.6 Very good
Parking
Free Wi-Fi
Pool
Spa
New York LaGuardia
Meals not included
3 nights + flight
C$ 631
Sonesta Resort Hilton Head Island - Hilton Head Island - Lounge
Sonesta Resort Hilton Head Island - Hilton Head Island - Lounge
Sonesta Resort Hilton Head Island
8.2 Very good
Pool
Pet friendly
Spa
Minneapolis St Paul
Meals not included
3 nights + flight
C$ 711
The Cottages by Spinnaker Resorts - Hilton Head Island - Bedroom
The Cottages by Spinnaker Resorts - Hilton Head Island - Bedroom
The Cottages by Spinnaker Resorts
1 Poor
Parking
Free Wi-Fi
Pool
New York LaGuardia
Meals not included
3 nights + flight
C$ 702
Hampton Inn Hilton Head - Hilton Head Island - Pool
Hampton Inn Hilton Head - Hilton Head Island - Pool
Hampton Inn Hilton Head
8 Very good
Parking
Free Wi-Fi
Pool
Pet friendly
Hartford Bradley Intl
Breakfast
3 nights + flight
C$ 509
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
6.2 Okay
Parking
Free Wi-Fi
Pool
Pet friendly
New York LaGuardia
Meals not included
3 nights + flight
C$ 391
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
8 Very good
Free Wi-Fi
Pool
New York LaGuardia
Meals not included
3 nights + flight
C$ 639
Go to map

Search by stars

2+ stars3+ stars4+ stars

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by board

BreakfastHalf boardSelf cateringAll inclusiveMeals not included

Search by price

C$ 392 - C$ 2,206C$ 2,206 - C$ 4,020C$ 4,020 - C$ 5,835C$ 5,835 - C$ 7,649C$ 7,649+ 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.