Westside Vacations from $593

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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.
Andrew Pinckney Inn

Andrew Pinckney Inn

4 out of 5
Charleston Historic District
Save 100% on your flight
Price was $808, price is now $593 per person
$593
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Charleston (CHS)
9.6/10 Exceptional! (1,370 reviews)
The staff was very friendly snd helpful. Great location downtown.

Reviewed on Sep 4, 2025

The Francis Marion Hotel

The Francis Marion Hotel

4 out of 5
Charleston Historic District
Save 100% on your flight
Price was $1,004, price is now $622 per person
$622
per person
Oct 30 - Nov 3
found 13 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Charleston (CHS)
9/10 Wonderful! (1,840 reviews)
Loved the whole experience. Valet parking was great. Loved the atmosphere of the hotel. Will be back soon.

Reviewed on Sep 2, 2025

Planters Inn

Planters Inn

4.5 out of 5
Charleston Historic District
Save 100% on your flight
Price was $2,576, price is now $1,698 per person
$1,698
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charleston (CHS)
9.4/10 Exceptional! (1,000 reviews)
Planters Inn was SO nice and I would highly recommend for anyone looking to stay in downtown Charleston. The rooms are large and spacious, unique, charming, and the beds are super comfy. The hotel staff was very helpful and it's within walking distance of King Street, French Quarter and all the historic sights around Charleston!

Reviewed on Sep 3, 2025

The Ryder Hotel

The Ryder Hotel

3.5 out of 5
Charleston Historic District
Save 100% on your flight
Price was $976, price is now $654 per person
$654
per person
Nov 8 - Nov 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
8.6/10 Excellent! (1,017 reviews)
It was a great location to do anything I wanted to do in downtown Charleston

Reviewed on Sep 3, 2025

The Restoration

The Restoration

4 out of 5
Charleston Historic District
Save 100% on your flight
Price was $1,072, price is now $766 per person
$766
per person
Nov 8 - Nov 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
9.6/10 Exceptional! (1,018 reviews)
I don’t know that I’ve ever stayed in a nicer place. This was an amazing stay in a great area of Charleston. The hotel even offered complementary shuttle service to a restaurant of our choice which we thought was pretty cool if you ever have the chance to stay at The Restoration I would definitely do it!

Reviewed on Sep 4, 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
$125 nightly
The price is $142 total per night from Sep 7 to Sep 8
$142 total
Sep 7 - Sep 8
Total with taxes and fees
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
$185 nightly
The price is $211 total per night from Sep 21 to Sep 22
$211 total
Sep 21 - Sep 22
Total with taxes and fees
Charleston Marriott
Drury Plaza Hotel North Charleston

Drury Plaza Hotel North Charleston

3 out of 5
West Montague Avenue, 2934, North Charleston, SC
Fully refundableReserve now, pay when you stay
$120 nightly
The price is $137 total per night from Sep 21 to Sep 22
$137 total
Sep 21 - Sep 22
Total with taxes and fees
Drury Plaza Hotel North Charleston
See all 6,823 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 stunning cathedral or amble around its beautiful beaches.

Stoney Field

Things to do

Charleston: Schooner Sailing Harbor Tour & Dolphin Watch

Charleston: Schooner Sailing Harbor Tour & Dolphin Watch

$54
per adult
92% of travellers recommend
Charleston: Schooner Sailing Harbor Tour & Dolphin Watch
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
Charleston: Fort Sumter Entry Ticket with Roundtrip Ferry

Charleston: Fort Sumter Entry Ticket with Roundtrip Ferry

$40
per adult
94% of travellers recommend
Charleston: Fort Sumter Entry Ticket 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.