Chesapeake Vacations

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Chesapeake Vacation Packages

Chesapeake Hotel Deals

Embassy Suites Charleston
Embassy Suites Charleston
3.5 out of 5
300 Court St, Charleston, WV
Fully refundableReserve now, pay when you stay
The price is ₩178,521 per night from Jul 27 to Jul 28
₩178,521
₩201,728 total
Jul 27 - Jul 28
includes taxes & fees
8.4/10 Very Good! (1,200 reviews)
Nice hotel
"Great hotel in great location! Within walking distance to shopping and restaurants."

Reviewed on Jul 9, 2025

Embassy Suites Charleston
Holiday Inn Express Charleston-Civic Center by IHG
Holiday Inn Express Charleston-Civic Center by IHG
2.5 out of 5
100 Civic Center Drive, Charleston, WV
Fully refundable
The price is ₩120,088 per night from Jul 20 to Jul 21
₩120,088
₩135,699 total
Jul 20 - Jul 21
includes taxes & fees
8.6/10 Excellent! (1,083 reviews)
"Quiet area, kind staff, surprisingly good hot breakfast."

Reviewed on Jul 10, 2025

Holiday Inn Express Charleston-Civic Center by IHG
Charleston Marriott Town Center
Charleston Marriott Town Center
3.5 out of 5
200 Lee St E, Charleston, WV
Fully refundableReserve now, pay when you stay
The price is ₩151,488 per night from Jul 19 to Jul 20
₩151,488
₩171,183 total
Jul 19 - Jul 20
includes taxes & fees
8.2/10 Very Good! (1,003 reviews)
"Went to the hotel to stay for a Heart Concert. Although the hotel was crowded the staff was very efficient and helpful. Liked that is was right across the street from the show."

Reviewed on Jul 11, 2025

Charleston Marriott Town Center
See all 169 properties in Chesapeake
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.

Discover the most popular places to visit in Chesapeake

Clay Center for the Arts and Sciences

4.5/5(47 reviews)

You can enjoy a show at Clay Center for the Arts and Sciences during your stay in Charleston. While in this walkable area, find time to visit its casinos.

Clay Center for the Arts and Sciences

Laidley Field

3/5(1 review)

Explore the great outdoors at Laidley Field, a lovely green space in Charleston. While in this walkable area, find time to visit its casinos.

Laidley Field

Frequently asked questions

How much does a Chesapeake vacation package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a vacation to Chesapeake costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Chesapeake?
If you'd like to score a cheap Chesapeake vacation package, consider planning a trip in January, February and November. You'll usually find lower rates on hotels and airfares during these months --- ideal for travelers wishing to save money.
How many days is enough for Chesapeake?
Generally, a handful of days is enough to explore the main attractions during your Chesapeake vacation. However, if you prefer to have more time to chill out or go on day tours, consider extending your trip.
How to find the best Chesapeake package deals?
Use Expedia's handy filters to find some unbeatable Chesapeake package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Chesapeake package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Chesapeake vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically land a better deal than booking each component separately. And you'll still have the freedom to create a customized Chesapeake vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Chesapeake?
If you have your Chesapeake travel dates locked in, book early to grab some incredible deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Chesapeake?

  1. Choose your dates: The things you'd like to do in Chesapeake and your preferred season can help you decide when to get away.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and meals to experiences and flights. Your hotel will probably be the biggest expense during your trip to Chesapeake.
  3. Decide how many days away: Start by listing all the sights and activities you'd like to get to in Chesapeake. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to choose a Chesapeake vacation package that brings all your bookings together.

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