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Hilton Head Island Vacation Packages

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A coastal town with a lighthouse, marina, and golf course.

Hilton Head Island
South Carolina
United States of America
North America
Hotwire.com

Hilton Head Island Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.

Hotel Tybee

2.5 out of 5

Price was $636, price is now $496 per person

$496

per person

Nov 18 - Nov 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Savannah (SAV)

Book a stay at this beach hotel in Tybee Island. Enjoy 2 outdoor pools, a beach locale, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tybee Island Beach and South Beach are located nearby.

Olde Harbour Inn

4 out of 5

Save 100% on your flight

Price was $972, price is now $618 per person

$618

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Savannah (SAV)

Book a stay at this historic hotel in Savannah. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions River Street and City Market are located nearby.

Perry Lane Hotel, A Luxury Collection Hotel, Savannah

5 out of 5

Save 100% on your flight

Price was $1,174, price is now $813 per person

$813

per person

Nov 20 - Nov 23

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Savannah (SAV)

Book a stay at this luxury hotel in Savannah. Enjoy 3 bars/lounges, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions River Street and City Market are located nearby.

The hotel was first rate from start to finish. Help with the luggage, the champagne and other treats throughout the stay, staff are friendly and helpful. Could not fault the place our room was also wonderful, we did the chef tasting dinner and it was unbelievable, so much food, wine pairing was generous, staff were knowledgeable and friendly.

Reviewed on Oct 16, 2026

Godley Manor

3 out of 5

Price was $1,144, price is now $837 per person

$837

per person

Jan 4 - Jan 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Savannah (SAV)

Stay at this guesthouse in Savannah. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions River Street and Forsyth Park are located nearby.

We loved our stay at Godley Manor! Its location was close enough to all the fun attractions, while being far enough away to offer a quiet nights sleep. We highly recommend Godley Manor for a great place to stay in Savannah!

Reviewed on Oct 14, 2026

Sabal House

2 out of 5

Price was $927, price is now $691 per person

$691

per person

Jan 4 - Jan 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Savannah (SAV)

Stay at this hotel in Savannah. Enjoy free WiFi, free bicycles on site, and valet parking (surcharge). Popular attractions River Street and City Market are located nearby.

River Street Inn

4 out of 5

Price was $1,166, price is now $869 per person

$869

per person

Jan 1 - Jan 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Savannah (SAV)

Book a stay at this luxury hotel in Savannah. Enjoy free WiFi, 3 restaurants, and 3 bars/lounges. Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions River Street and City Market are located nearby.

The Ann Savannah, Apartments By Marriott Bonvoy

4 out of 5

Price was $890, price is now $676 per person

$676

per person

Jan 1 - Jan 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Savannah (SAV)

Stay at this aparthotel in Savannah. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Popular attractions River Street and City Market are located nearby.

Boardwalk & Blue by Avantstay Sleeps 22 Infinity Pool + Elevator + Pool Table Steps to Sand

3 out of 5

Save 100% on your flight

Price was $6,266, price is now $4,757 per person

$4,757

per person

Dec 29 - Jan 2

found 1 day ago

Roundtrip non-stop flight included

Indianapolis (IND) to Savannah (SAV)

Stay at this cottage in Hilton Head Island. Enjoy free parking, a beach locale, and a pool table. Popular attractions Coligny Beach and Driessen Beach Park are located nearby.