Westside Vacations from $942

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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
Save 100% on your flight
$942
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charleston (CHS)
8.8/10 Excellent! (1,121 reviews)
137 Grand Pavilion by Avantstay Steps to Beach + Resort Pools Wild Dunes Gated

137 Grand Pavilion by Avantstay Steps to Beach + Resort Pools Wild Dunes Gated

Save 100% on your flight
$1,986
per person
Oct 12 - Oct 17
found 14 hours ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
No reviews
The Charleston Place

The Charleston Place

Charleston Historic District
Save 100% on your flight
$1,862
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charleston (CHS)
9.6/10 Exceptional! (1,008 reviews)
Oceanfront w/ Pool, Panoramic Deck Views, 5bdr Folly Ocean Breeze by Avantstay

Oceanfront w/ Pool, Panoramic Deck Views, 5bdr Folly Ocean Breeze by Avantstay

Save 100% on your flight
$2,104
per person
Oct 18 - Oct 21
found 11 hours ago
Roundtrip flight included
Philadelphia (PHL) to Charleston (CHS)
No reviews
Poseidon By Avantstay On The Beach! Two Ocean Facing Balconies & Hot Tub

Poseidon By Avantstay On The Beach! Two Ocean Facing Balconies & Hot Tub

Sunset Point
Save 100% on your flight
$1,458
per person
Oct 18 - Oct 21
found 11 hours ago
Roundtrip flight included
Philadelphia (PHL) 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 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.

A garden pathway surrounded by lush greenery and stone structures.

Harleston Village

If you're spending some time in Harleston Village, Marion Square and The Riviera Theater are top sights worth seeing.

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
$121 nightly
$137 total
Sep 1 - Sep 2
Total with taxes and fees
8/10 Very Good! (1,262 reviews)
"Could use an update, halls smelled and carpet look dirty. Staff except for lady at check in was not very helpful. Breakfast was good, hard to get a place to sit on the weekends, didn't use outdoor pool."

Reviewed on Aug 24, 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
$146 nightly
$166 total
Sep 1 - Sep 2
Total with taxes and fees
Charleston Marriott
The Francis Marion Hotel

The Francis Marion Hotel

387 King St Charleston SC
$195 nightly
$222 total
Aug 27 - Aug 28
Total with taxes and fees
The Francis Marion Hotel
See all 6,792 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

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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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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Stoney Field

Explore the great outdoors at Stoney Field, a lovely green space in Charleston. Visit the area's churches 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 churches.
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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 Entry Ticket with Roundtrip Ferry

$43
per adult
98% of travellers recommend
Charleston: Fort Sumter Entry Ticket 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.