Westside Vacation Packages

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

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Top Holiday Package Deals in Westside

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 $858, price is now CA $726 per person
CA $726
per person
Dec 20 - Dec 22
found 24 hours ago
Roundtrip flight included
Detroit (DTW) to Charleston (CHS)
8.8/10 Excellent! (1,241 reviews)

The Charleston Place

The Charleston Place

5 out of 5
Charleston Historic District
Price was CA $1,456, price is now CA $1,278 per person
CA $1,278
per person
Dec 20 - Dec 22
found 24 hours ago
Roundtrip flight included
Detroit (DTW) to Charleston (CHS)
9.6/10 Exceptional! (1,003 reviews)

The Ansonborough

The Ansonborough

4 out of 5
Charleston Historic District
Price was CA $1,975, price is now CA $1,770 per person
CA $1,770
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Charleston (CHS)
9.4/10 Exceptional! (1,187 reviews)

Emeline

Emeline

4 out of 5
Charleston Historic District
Price was CA $866, price is now CA $777 per person
CA $777
per person
Dec 20 - Dec 22
found 24 hours ago
Roundtrip flight included
Detroit (DTW) to Charleston (CHS)
9.4/10 Exceptional! (1,779 reviews)
Everything was nice. Everything looked clean but our bed sheets had blood on them from the previous occupants. It was on the side by the wall on the edge. Not easily seen. Obviously they were not changed after the last people checked out.

Reviewed on Oct 26, 2026

The Restoration

The Restoration

4 out of 5
Charleston Historic District
Price was CA $1,303, price is now CA $1,198 per person
CA $1,198
per person
Dec 20 - Dec 22
found 24 hours ago
Roundtrip flight included
Detroit (DTW) to Charleston (CHS)
9.6/10 Exceptional! (1,269 reviews)
We had an amazing stay. However, we personally witnessed rooms on the other side of the building suffering massive water damage during a downpour.

Reviewed on Oct 26, 2026

Where to stay in Westside

Find the best Westside areas and neighborhoods for the activities you enjoy most. Learn more about Westside
A street lined with historic buildings, parked cars, and palm trees.

Charleston Historic District

5 out of top 10 points of interest in this area

Explore this National Historic Landmark District, boasting an unparalleled collection of 18th and 19th-century architecture, including Charleston "single houses." Nearby Ansonborough features fine Greek Revival houses and historic civic buildings.

Find hotels in Charleston Historic District

Westside Hotel Deals

Holiday Inn Express & Suites Charleston DWTN - Medical CTR by IHG

Holiday Inn Express & Suites Charleston DWTN - Medical CTR by IHG

2.5 out of 5
250 Spring Street Charleston SC
Fully refundable
The price is CA $160 per night from Nov 15 to Nov 16
CA $160
CA $199 total
Nov 15 - Nov 16
includes taxes & fees
8/10 Very good! (1,228 reviews)
"Breakfast was honestly the best I’ve ever had at a hotel. The rooms were clean and modern. Loved the location as well!"

Reviewed on Oct 25, 2026

Holiday Inn Express & Suites Charleston DWTN - Medical CTR by IHG
Charleston Marriott

Charleston Marriott

3.5 out of 5
170 Lockwood Blvd Charleston SC
The price is CA $249 per night from Nov 15 to Nov 16
CA $249
CA $287 total
Nov 15 - Nov 16
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"Our room was beautiful and exactly what we hoped for. The breakfast was delicious and the staff friendly and helpful. It was a convenient location, both in the water and close to the downtown area."

Reviewed on Oct 19, 2026

Charleston Marriott
The Francis Marion Hotel

The Francis Marion Hotel

4 out of 5
387 King St Charleston SC
The price is CA $281 per night from Nov 26 to Nov 27
CA $281
CA $320 total
Nov 26 - Nov 27
includes taxes & fees
9/10 Wonderful! (2,632 reviews)
"The room was extremely clean. Water in the fridge was a nice perk, although we did not get water bottles on the 3rd day. Bed and pillows are excellent. We didn’t want to invest a lot of money and time on breakfast, but we discovered a Chick-fil-A less than a block away which was perfect for us. The ..."

Reviewed on Oct 26, 2026

The Francis Marion Hotel
See all 6,775 properties in Westside
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.
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Frequently asked questions

How much does a Westside vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in Westside from just CA $726. And the more you bundle, the more money you save. Your dream vacation has never been more affordable.
How do I get a cheap travel package to Westside?
Our Westside vacation packages mean plenty of savings for the savvy wanderer. For the best deal, simply combine your flights, hotels and activities into a convenient package. But bargain prices are only the start of your next epic adventure. When you book with Expedia, you'll have more than 550 airlines and 1,000,000 hotels all over the world to choose from. Whatever your budget, there's a vacation package to suit you.
Where should I stay in Westside?
With fascinating attractions like Port of Charleston Cruise Terminal and Charleston City Market in this area, look for a hotel located near either one. College of Charleston is another sight in Westside that people flock to.
What are the top hotels in Westside?
Book a room at Spacious Apartment Downtown. It's one of this neighborhood's most popular properties. Another top option in Westside is The Condon Carriage House By Stayduvet.
How far in advance should I book my Westside vacation?
It's difficult to pick the best time for airfares, but we generally suggest the earlier, the better. Most international flights on Expedia become available up to 12 months in advance. If you're booking at the last minute, fear not. Budget prices appear from time to time just weeks before departure dates.
What does an Expedia Westside travel package include?
That mostly depends on you. You can pick from a range of Westside bundles, such as a hotel, flight and rental car. You can also book a flight and a hotel, or a flight and a rental car. Once you've made your booking, you can add on the fun stuff like tours and activities. Whatever your ideal Westside escape looks like, get set to save!
What should I know before booking a Westside travel package?
Tailor deals that suit your budget with an Expedia package. Hotels, airfares, rental cars — we've got all of them. You'll save loads just by combining your bookings. Whether you're taking off on a ski trip or drinking cocktails on a beach, your ideal vacation is just a few clicks away.
Can I choose my airline with a Westside Expedia vacation package?
Most definitely. Expedia has more than 550 airline partners to pick from all over the world. With all that choice at your fingertips, finding the perfect carrier to fly you to Westside will be a cinch.
If I'm not able to travel, can I cancel my Westside vacation package?
Whether it's your hotel or flight, you can cancel or change it. Locked in your Westside vacation package in the last 24 hours? You may be able to make changes or cancellations for free. For older bookings, you may be charged a fee by your hotel, airline or car rental company. For more information, visit our Customer Service Portal. We're here to help you every step of the way.

Stay near popular Westside attractions

Joseph P. Riley, Jr. Park

Catch an event at Joseph P. Riley, Jr. Park during your trip to Charleston. Wander the area's beautiful beaches or simply enjoy one of its top-notch restaurants.
See properties

Things to do

Charleston: Historical Downtown Tour by Horse-drawn Carriage

Charleston: Historical Downtown Tour by Horse-drawn Carriage

CA $71
per adult
96% of travellers recommend
Charleston: Historical Downtown Tour by Horse-drawn Carriage
Charleston: Fort Sumter Entry Ticket with Roundtrip Ferry

Charleston: Fort Sumter Access with Roundtrip Ferry

CA $64
per adult
98% of travellers recommend
Charleston: Fort Sumter Access with Roundtrip Ferry
Old Town Trolley Tour of Charleston

Old Town Trolley Tour of Charleston

CA $57
per adult
90% of travellers recommend
Old Town Trolley Tour of Charleston
See all activities in Charleston
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.