A sunset over a calm lake with tall trees reflected in the water.

Charleston Vacations from $548

Book a Hotel + Flight or Car together to unlock savings

The Latest Charleston Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 28 - Jan 31

    Larkspur Landing Extended Stay Suites St. Louis Riverport - Airport West + Flight

    Riverport
    3 nights
    3.0 star property
    7.8/10 - Good (1,006 reviews)
    Roundtrip • New York (EWR) - St. Louis (STL)
    EWR - STL • Nonstop STL - EWR • Nonstop
    $639
    $548
    per traveler
    found 1 day ago
    Larkspur Landing Extended Stay Suites St. Louis Riverport - Airport West
  • Jan 28 - Jan 31

    The Wildwood Hotel + Flight

    Wildwood
    3 nights
    3.5 star property
    9.2/10 - Wonderful (1,683 reviews)
    Roundtrip • New York (EWR) - St. Louis (STL)
    EWR - STL • Nonstop STL - EWR • Nonstop
    $859
    $584
    per traveler
    found 1 day ago
    The Wildwood Hotel
  • Jan 28 - Jan 31

    Remodeled and Inviting Free EV + Flight

    Fenton
    3 nights
    2.0 star property
    9.4/10 - Exceptional (3 reviews)
    "We had a great time with my family ❤️ thank you"
    Reviewed October 12, 2026
    Roundtrip • New York (EWR) - St. Louis (STL)
    EWR - STL • Nonstop STL - EWR • Nonstop
    $922
    $678
    per traveler
    found 1 day ago
    Remodeled and Inviting Free EV
  • Jan 28 - Jan 31

    The Cheshire + Flight

    Richmond Heights
    3 nights
    4.0 star property
    8.8/10 - Excellent (1,006 reviews)
    "A wonderful break from boring hotels! My kids loved all the artwork and the scavenger hunt. The pub food and drinks were fantastic, as was the hotel breakfast each morning. We will definitely plan to return."
    Reviewed November 9, 2026
    Roundtrip • New York (EWR) - St. Louis (STL)
    EWR - STL • Nonstop STL - EWR • Nonstop
    $820
    $679
    per traveler
    found 1 day ago
    The Cheshire
  • Jan 28 - Jan 31

    Ameristar Casino Resort and Spa + Flight

    St. Charles
    3 nights
    4.5 star property
    8.6/10 - Excellent (1,094 reviews)
    "We were here for a wedding. Our room was very nice but my son’s bathroom was disgusting and not clean, they had to switch rooms and the only compensation they gave them was a food voucher. Not acceptable with blood and vomit not cleaned from previous guest. We expected more for this caliber of hotel."
    Reviewed November 8, 2026
    Roundtrip • New York (EWR) - St. Louis (STL)
    EWR - STL • Nonstop STL - EWR • Nonstop
    $860
    $721
    per traveler
    found 1 day ago
    Ameristar Casino Resort and Spa

Where to stay in and around Charleston

Explore the charm of Charleston, MO, where historic districts and outdoor adventures await. Don’t miss the picturesque downtown Sikeston and local country stores for a taste of friendly hospitality. Experience a delightful blend of family-friendly vibes and scenic beauty in this inviting region.

Sikeston

For travelers seeking a blend of family-friendly activities and budget-friendly options, Sikeston serves as an excellent base for exploring the nearby charm of Charleston, Missouri. Visitors can enjoy the vibrant recreational areas, try their luck at the local casino, or immerse themselves in the arts at the Sikeston Depot Museum. With Central Park providing a perfect spot for relaxation, Sikeston is about a 14-mile drive from Charleston, making it a smart choice for your stay in the region.

Bertrand

Experience the charm of Bertrand, a welcoming hub for families and nature enthusiasts eager to explore the surrounding beauty. This city offers access to a variety of outdoor activities, including golfing and scenic adventures at local parks and lakes. Just 6 miles from Charleston, Bertrand provides a convenient base for visiting attractions like the City of Miner Convention Center and the Sikeston Depot Museum. Choose Bertrand for your stay and immerse yourself in its delightful offerings and natural landscapes.

Diehlstadt

If you are a family-oriented traveler, look no further than Diehlstadt, a charming village in Charleston, Missouri, which features delightful attractions like the City of Miner Convention Center for events, the Front Street Studio & Art Gallery for a dose of creativity, and the Sikeston Depot Museum for a peek into local history. With visitor numbers peaking in March and June to July, Diehlstadt offers a welcoming atmosphere year-round. This location ensures easy access to nearby sites, making it a smart choice for your hotel stay.

Anniston

Anniston stands out as a prime spot for travelers interested in a mix of outdoor and city experiences. This charming city offers easy access to local landmarks like the Columbus-Belmont State Park, the Sikeston Depot Museum, and the City of Miner Convention Center, making it ideal for family getaways or business trips. With its proximity, about 7 miles from Charleston, Anniston is a smart choice for a hotel stay, providing a perfect base to explore the region's attractions.

Wilson City

Travelers visiting Charleston, Missouri, will find Wilson City to be the ideal base for their vacation, featuring a rich blend of family-friendly activities and natural beauty. Nature enthusiasts can explore the historic Fort Defiance State Park, the serene Ballard Wildlife Management Area, and the scenic Columbus-Belmont State Park, making it perfect for outdoor adventures. Located about 7 miles from Charleston, Wilson City offers a smart choice for budget-conscious visitors seeking a peaceful retreat without straying far from the action.

Charleston Hotel Deals

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.

Frequently Asked Questions

What's the best vacation package for Charleston?

For families seeking the best vacation packages in Charleston, a stay at Super 8 by Wyndham Charleston/Sikeston East MO offers a practical base. Located about 1 mile from central Charleston, this hotel features family rooms and free breakfast, making mornings easier before heading out to explore. Travelers often praise the big rooms and helpful staff, which helps make for a comfortable stay for everyone.


Travelers looking for a value-focused Charleston vacation package will find Super 8 by Wyndham Charleston/Sikeston East MO to be a solid choice. It provides free breakfast and free WiFi, adding convenience and helping to keep costs down. Guests frequently highlight the good breakfast and helpful staff, contributing to a pleasant and budget-friendly experience.


Couples planning a romantic getaway to Charleston can consider a package with a stay at Super 8 by Wyndham Charleston/Sikeston East MO as a convenient starting point for exploring the area's natural beauty. Its location provides easy access to outdoor attractions like Big Oak Tree State Park, about 6 miles away, or Reelfoot Lake, about 38 miles away, both offering scenic spots for a romantic outing. The hotel's free breakfast also allows for relaxed mornings before venturing out.

How can I save money on a Charleston vacation package?

When you bundle, you can save up to 30%*. To save money on a Charleston package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

What are the top things to do in Charleston?

A Charleston vacation offers a blend of outdoor adventure and local culture, making it ideal for exploring nature and historical sites:


Browse and book things to do in Charleston on Expedia.

Do you need to rent a car in Charleston, or is public transport enough?

For Charleston vacation packages with flights, a rental car is highly recommended. Charleston is an outdoor and nature destination outside a city, with attractions spread out across the area.


Jackson, TN (MKL-McKellar-Sipes Regional) is the primary airport, located about 94 miles from central Charleston, making a car essential for convenient travel from the airport and for exploring the various state parks and natural sites. A Charleston vacation package does not automatically include transportation, so planning for a rental car will offer the most flexibility.

Can I change or cancel my Charleston vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking Charleston vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Does Expedia offer Book Now, Pay Later Charleston vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Charleston vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to Charleston?

To find last-minute vacation packages to Charleston, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on Charleston vacation packages?

Free cancellation on a Charleston vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a Charleston vacation as a package or separately?

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Charleston getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my Charleston vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.