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Vacations in Hilton Head Island

Vacations in Hilton Head Island

2 travellers

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Cheap Hilton Head Island package deals

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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
8.9 Very good
Free Wi-Fi
Pool
Boston Logan Intl
Meals not included
3 nights + flight
C$ 1,125
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
Boston Logan Intl
Breakfast
3 nights + flight
C$ 810
Pool
Pet friendly
Boston Logan Intl
Meals not included
3 nights + flight
C$ 1,255
Parking
Free Wi-Fi
Pool
Pet friendly
Philadelphia
Breakfast
3 nights + flight
C$ 1,005
Free Wi-Fi
Pool
Albuquerque
Meals not included
3 nights + flight
C$ 1,293
Parking
Free Wi-Fi
Pool
Boston Logan Intl
Meals not included
3 nights + flight
C$ 563
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
Free Wi-Fi
Pool
Boston Logan Intl
Meals not included
3 nights + flight
C$ 835
Free Wi-Fi
Pool
Pet friendly
Spa
Albuquerque
Meals not included
3 nights + flight
C$ 1,457
Players Club Resort - Hilton Head Island - Patio
Players Club Resort - Hilton Head Island - Patio
Players Club Resort
8.5 Very good
Parking
Free Wi-Fi
Pool
Philadelphia
Meals not included
3 nights + flight
C$ 1,140
Parking
Free Wi-Fi
Pool
Pet friendly
Boston Logan Intl
Meals not included
3 nights + flight
C$ 792
The Spa 1219 - Hilton Head Island - Living room
The Spa 1219 - Hilton Head Island - Living room
The Spa 1219
Pool
Boston Logan Intl
Meals not included
3 nights + flight
C$ 1,011
Pool
Pet friendly
Spa
Boston Logan Intl
Meals not included
3 nights + flight
C$ 1,214
Parking
Free Wi-Fi
Pool
Pet friendly
Boston Logan Intl
Breakfast
3 nights + flight
C$ 853
Simple Rewards Inn - Hilton Head Island - Building
Simple Rewards Inn - Hilton Head Island - Building
Simple Rewards Inn
8.3 Very good
Parking
Free Wi-Fi
Pet friendly
Boston Logan Intl
Meals not included
3 nights + flight
C$ 489
Parking
Free Wi-Fi
Pool
Pet friendly
Boston Logan Intl
Meals not included
3 nights + flight
C$ 541
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
8.5 Very good
Free Wi-Fi
Pool
Boston Logan Intl
Meals not included
3 nights + flight
C$ 867

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.