Uptown Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Top Holiday Package Deals in Uptown

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

The Ryder Hotel

3.5 out of 5
Charleston Historic District
Price was CA $2,142, price is now CA $1,639 per person
CA $1,639
per person
Dec 27 - Dec 31
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Charleston (CHS)
8.8/10 Excellent! (1,241 reviews)
Bed was very comfortable and the Christmas decorations were adorable

Reviewed on Nov 9, 2026

Seawatch at Island Club

Seawatch at Island Club

3 out of 5
Mid Island
Price was CA $2,936, price is now CA $2,158 per person
CA $2,158
per person
Dec 27 - Jan 1
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Savannah (SAV)
9.2/10 Wonderful! (56 reviews)
We were very impressed with the property and view of the Atlantic Ocean. All beds were very comfortable. Overall it was a wonderful place to stay for three days of family events. We will return. Thanks

Reviewed on Nov 3, 2026

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

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

3 out of 5
Mid Island
Price was CA $10,110, price is now CA $7,759 per person
CA $7,759
per person
Dec 27 - Jan 1
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Savannah (SAV)
No reviews

The Grand Sandcastle by Avantstay Sleeps 22 Covered Pool Walk to Beach

The Grand Sandcastle by Avantstay Sleeps 22 Covered Pool Walk to Beach

3 out of 5
Mid Island
Price was CA $9,704, price is now CA $7,459 per person
CA $7,459
per person
Dec 26 - Jan 2
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Savannah (SAV)
No reviews

JW Marriott Savannah Plant Riverside District

JW Marriott Savannah Plant Riverside District

5 out of 5
Historic Downtown Savannah
Price was CA $2,148, price is now CA $1,778 per person
CA $1,778
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Savannah (SAV)
9.4/10 Exceptional! (1,576 reviews)
Cool place. However, Extra unannounced ‘amenities fees’ (a significant added cost) were learned about only upon checkout. These amenities were not disclosed to us as available options any time during our stay - until checkout.

Reviewed on Nov 11, 2026

Where to stay in Uptown

Find the best Uptown areas and neighborhoods for the activities you enjoy most. Learn more about Uptown
An aerial view of a coastal town with a marina, dense greenery, and a bridge connecting to the mainland.

Historic District

5 out of top 10 points of interest in this area

If you're spending some time in Historic District, USCB Center for the Arts and Bay Street are top sights worth seeing.

Find hotels in Historic District

Uptown Hotel Deals

Hotel Carolina

Hotel Carolina

2 out of 5
9 Marina Side Drive Hilton Head Island SC
Fully refundableReserve now, pay when you stay
The price is CA $91 per night from Nov 12 to Nov 13
CA $91
CA $101 total
Nov 12 - Nov 13
includes taxes & fees
8/10 Very good! (213 reviews)
"It felt just like I remember Hilton Head Island back when beach and family were all that mattersef. No fuss, no insane fees, no rude employees! Breath of fresh air!"

Reviewed on Nov 8, 2026

Hotel Carolina
The Westin Hilton Head Island Resort & Spa

The Westin Hilton Head Island Resort & Spa

4 out of 5
2 Grasslawn Ave Hilton Head Island SC
Get rates
The Westin Hilton Head Island Resort & Spa
Beaufort Cottage: Pet-friendly Near Parris Island!

Beaufort Cottage: Pet-friendly Near Parris Island!

3 out of 5
Beaufort SC
9.6/10 Exceptional! (5 reviews)
"Very convenient cottage while in town for Pariss Island Graduation. There was plenty of room for me and my wife as well as my mother in law and for one night, our marine. We highly recommend this cottage to other families visiting Parris Island and/or Beaufort."

Reviewed on Oct 5, 2026

Get rates
Beaufort Cottage: Pet-friendly Near Parris Island!
See all 4,698 properties in Uptown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does an Uptown vacation package cost?
From as low as CA $1,639. Yes, you read that correctly. Our Uptown packages are a great way to make your budget stretch further. Combine your favorite hotels, flights and rental car and get out and explore this exciting destination.
How do I get a cheap travel package to Uptown?
If you love scoring a bargain, bundle your bookings into an Uptown vacation package. Whether you're searching for hotels, flights, day tours or rental cars, you can book everything in one place. You'll have endless choice at your fingertips as well. Expedia has over 550 partner airlines and 1,000,000 hotels worldwide to select from. Fly with who you want, stay anywhere you like and save some cash — now that's the perfect vacation!
Where should I stay in Uptown?
With popular attractions like Bay Street and Henry C. Chambers Waterfront Park in this neighborhood, look for a hotel situated near them. University of South Carolina-Beaufort is another sight in Uptown that visitors flock to.
What are the top hotels in Uptown?
Get your escape off to a good start by booking a room at Perfect In Historic Downtown Beaufort + 2 Bikes. Checkout Our Reviews. It's one of most popular hotels in Uptown. Another cozy option is Original Craftsman Cottage.
How far in advance should I book my Uptown vacation?
To score rock-bottom prices, book ASAP. Air carriers typically release flights, along with some of the lowest fares, up to 12 months prior to departure. Hotels, car rental and experiences should also be booked early to avoid disappointment. If you're in need of a last-minute getaway in Uptown, there are always plenty of great bargains to be had on Expedia. Book your escape today!
What does an Expedia Uptown travel package include?
It comes down to what sort of getaway you want to have. Uptown travel deals can include car rentals, hotels and flights. You can mix and match to find the travel package that suits your needs. You can also add on activities and experiences after you've booked to get even bigger discounts.
What should I know before booking an Uptown travel package?
You can save big by combining your flights, hotels and rental cars. Once you've made your booking, add on fun stuff like activities or tours. Your next unforgettable vacation is only a few clicks away.
Can I choose my airline with an Uptown Expedia vacation package?
Yes, definitely. Expedia has over 550 airline partners to pick from all over the world. With so many choices, finding the right carrier to bring you to Uptown will be a cinch.
If I'm not able to travel, can I cancel my Uptown vacation package?
Plans can change unexpectedly, so yes, you can. You may be able to cancel or amend your Uptown vacation package for free if you've booked in the last 24 hours. For older bookings, you can still cancel and rebook, but your hotel, car rental company or airline may charge a fee. Looking for more information? Look up our Customer Service Portal. We'll help make sure your getaway goes off without a hitch.

Things to do

Hilton Head Island: Sunset Dolphin Cruise

Hilton Head Island: Sunset Dolphin Cruise

CA $71
per adult
98% of travellers recommend
Hilton Head Island: Sunset Dolphin Cruise
Hilton Head Island: Dolphin Watching Cruise with Donuts

Hilton Head Island: Dolphin Watching Cruise with Donuts

CA $83
per adult
Hilton Head Island: Dolphin Watching Cruise with Donuts
Picture 10 for Activity Hilton Head Island: Disappearing Island and Dolphin Tour

Hilton Head Island: Disappearing Island and Dolphin Tour

CA $78
per adult
Hilton Head Island: Disappearing Island and Dolphin Tour
See all activities in Beaufort
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.