Westside Vacations from $214

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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.
DoubleTree by Hilton Charleston Mount Pleasant

DoubleTree by Hilton Charleston Mount Pleasant

4 out of 5
Price was $311, price is now $214 per person
$214
per person
Dec 14 - Dec 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
9.2/10 Wonderful! (1,014 reviews)
Bathroom fan didn't work, empty body wash dispenser, but a nice room overall. Great location for our 4 day stay.

Reviewed on Oct 28, 2025

King 583

King 583

2 out of 5
Downtown Charleston
Save 100% on your flight
Price was $536, price is now $344 per person
$344
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
9/10 Wonderful! (172 reviews)
Room was great, staff was really nice at greeting us and making sure we had everything we needed, enjoyed being able to text the staff if we had a question etc. it was a perfect honeymoon

Reviewed on Oct 22, 2025

The Francis Marion Hotel

The Francis Marion Hotel

4 out of 5
Charleston Historic District
Save 100% on your flight
Price was $602, price is now $387 per person
$387
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
9/10 Wonderful! (1,902 reviews)
Stay was great! Great location and walkable area

Reviewed on Oct 29, 2025

Emeline

Emeline

4 out of 5
Charleston Historic District
Save 100% on your flight
Price was $736, price is now $503 per person
$503
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
9.4/10 Exceptional! (1,672 reviews)
Rooms are super small, but well kept and the hotel had a wonderful atmosphere and was perfectly positioned for walking around the shopping and dining areas.

Reviewed on Oct 27, 2025

Planters Inn

Planters Inn

4.5 out of 5
Charleston Historic District
Save 100% on your flight
Price was $909, price is now $622 per person
$622
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
9.6/10 Exceptional! (1,008 reviews)
Hotel staff were always available and accommodating. Excellent service in all respects.

Reviewed on Oct 30, 2025

Where to stay in Westside

Find the best Westside areas and neighborhoods for the activities you enjoy most. Learn more about Westside
Charleston Historic District showing heritage architecture

Charleston Historic District

4 out of top 10 points of interest in this area
4.5/5(3,245 area reviews)

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 - Westedge by IHG

Holiday Inn Express & Suites Charleston Dwtn - Westedge by IHG

2.5 out of 5
250 Spring Street, Charleston, SC
Fully refundable
$108 nightly
The price is $123 total per night from Nov 23 to Nov 24
$123 total
Nov 23 - Nov 24
Total with taxes and fees
8/10 Very Good! (1,422 reviews)
The staff was great very personable and helpful.

Reviewed on Oct 26, 2025

Holiday Inn Express & Suites Charleston Dwtn - Westedge by IHG
Charleston Marriott

Charleston Marriott

3.5 out of 5
170 Lockwood Blvd, Charleston, SC
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $158 total per night from Nov 24 to Nov 25
$158 total
Nov 24 - Nov 25
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
Very friendly and helpful staff, the pool area is beautiful. The lobby has a nice view of the river. Parking is in the back of the hotel, the extra cost for valet is likely worth it.

Reviewed on Oct 6, 2025

Charleston Marriott
Courtyard by Marriott Charleston-North Charleston

Courtyard by Marriott Charleston-North Charleston

3 out of 5
7465 NORTHSIDE DR, North Charleston, SC
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $114 total per night from Nov 2 to Nov 3
$114 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (1,016 reviews)
Amazing room great check in staff great Bistro Very clean linen. Wish we had a microwave!

Reviewed on Oct 28, 2025

Courtyard by Marriott Charleston-North Charleston
See all 6,507 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Westside

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.

Joseph P. Riley, Jr. Park

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.

Johnson Hagood Memorial Stadium

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.

Stoney Field

Things to do

Schooner Pride

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

$44
per adult
94% of travellers recommend
Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor
Charleston: Daytime or Sunset Historic Harbor Cruise

Charleston: Daytime or Sunset Historic Harbor Cruise

$50
per adult
86% of travellers recommend
Charleston: Daytime or Sunset Historic Harbor Cruise
Fort Sumter Admission and Self-Guided Tour with Roundtrip Ferry

Fort Sumter Admission and Self-Guided Tour with Roundtrip Ferry

$40
per adult
84% of travellers recommend
Fort Sumter Admission and Self-Guided Tour with Roundtrip Ferry
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.