Westside Vacations from $599

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Your Westside Vacation

Booking a Westside vacation package is a superb way to get to know the ins and outs of this neighborhood. From its renowned sites to its lesser-known gems, you'll be sure to uncover something new. Some popular nearby attractions to check out during your trip to Westside include USS Yorktown, Charleston City Market and College of Charleston. Don't just wish for it — take action! Reserve your ideal Westside vacation with Expedia and travel your way.

The Latest Westside Vacation Packages

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

The Ryder Hotel

Charleston Historic District
$599
per person
Jan 15 - Jan 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
8.8/10 Excellent! (1,241 reviews)
The Charleston Place

The Charleston Place

Charleston Historic District
Save 100% on your flight
$2,395
per person
Dec 26 - Dec 31
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
9.6/10 Exceptional! (1,003 reviews)
The Pinch Hotel

The Pinch Hotel

Charleston Historic District
$727
per person
Jan 16 - Jan 19
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
9.8/10 Exceptional! (210 reviews)
Historic Retreat Near Beach w/ Pool 306 Charleston Blvd Roosevelt Retreat by Avantstay

Historic Retreat Near Beach w/ Pool 306 Charleston Blvd Roosevelt Retreat by Avantstay

Ocean Boulevard
Save 100% on your flight
$2,935
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Charleston (CHS)
No reviews
Landing Stylish 1bd, Gym

Landing Stylish 1bd, Gym

$875
per person
Dec 21 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charleston (CHS)
No reviews

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.

A historic pink building with green shutters, a black wrought iron fence, and lush greenery.

Downtown Charleston

3 out of top 10 points of interest in this area

Explore the National Historic Landmark District, boasting an unparalleled collection of 18th and 19th-century architecture, including Charleston "single houses." Discover fine Greek Revival homes in Ansonborough and historic civic buildings on Broad Street.

A waterfront promenade with palm trees, a row of elegant buildings, and a clear sky.

Cannonborough Elliotborough

While visiting Cannonborough Elliotborough, you might make a stop by sights like Upper King Design District and Karpeles Manuscript Library Museum.

A rustic cabin surrounded by tall trees in a forest.

West Ashley

Boasting Citadel Mall and Bon Secours St. Francis Hospital, this area is connected by the West Ashley Greenway and features historic sites like Magnolia Plantation and Gardens. Revitalization efforts attract art and design businesses.

A blue corner building with a street sign for King St.

King Street

While visiting King Street, you might make a stop by sights like Marion Square and Charleston Music Hall.

Westside Hotel Deals

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

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

250 Spring Street Charleston SC
Fully refundable
$125 nightly
$142 total
Nov 15 - Nov 16
Total with taxes and 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

170 Lockwood Blvd Charleston SC
Fully refundableReserve now, pay when you stay
$180 nightly
$205 total
Nov 15 - Nov 16
Total with taxes and 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

387 King St Charleston SC
$224 nightly
$255 total
Nov 24 - Nov 25
Total with taxes and fees
The Francis Marion Hotel
See all 6,764 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.

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.
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Brittlebank Park

After visiting Brittlebank Park, make a plan to see the other sights and activities in Charleston. Check out the stunning cathedral and lively bars in this walkable area.
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Johnson Hagood Memorial Stadium

Explore the great outdoors at Johnson Hagood Memorial Stadium, a lovely green space in Charleston. Visit the area's stunning cathedral or amble around its beautiful beaches.
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Harmon Field

After visiting Harmon Field, make a plan to see the other sights and activities in Charleston. Discover the area's acclaimed art scene and shops.
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Stoney Field

Explore the great outdoors at Stoney Field, a lovely green space in Charleston. Visit the area's shops or amble around its beautiful beaches.
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Things to do

Charleston: Historical Downtown Tour by Horse-drawn Carriage

Charleston: Historical Downtown Tour by Horse-drawn Carriage

$50
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

$46
per adult
98% of travellers recommend
Charleston: Fort Sumter Access with Roundtrip Ferry
Charleston: Daytime or Sunset Historic Harbor Cruise

Charleston: Daytime or Sunset Historic Harbor Cruise

$54
per adult
90% of travellers recommend
Charleston: Daytime or Sunset Historic Harbor Cruise
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.