Chesapeake Vacations

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Your Chesapeake Vacation

Food, history, entertainment and more … There's so much to discover with a Chesapeake vacation package. And with the ability to customize your city break, it's guaranteed to be one that's tough to forget. Cabin Creek Quilts is one of the famous attractions to put on your to-do list during a trip to Chesapeake. Your ultimate Chesapeake vacation is a couple of clicks away. Browse flights, accommodations and more on Expedia for an adventure that's tailored to suit your travel style.

Chesapeake Hotel Deals

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
$101 nightly
The price is $114 total per night from Jul 5 to Jul 6
$114 total
Jul 5 - Jul 6
Total with taxes and fees
8.6/10 Excellent! (1,157 reviews)
"I stayed 10 days and I was so impressed with the efficiency of the staff and the kindness they showed. My room was clean and neat as well as the hotel was well maintained. I will never stay at another hotel in Charleston other than the Holiday Inn express."

Reviewed on Jul 1, 2026

Holiday Inn Express Charleston-Civic Center by IHG
Embassy Suites Charleston

Embassy Suites Charleston

3.5 out of 5
300 Court St Charleston WV
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $138 total per night from Jul 12 to Jul 13
$138 total
Jul 12 - Jul 13
Total with taxes and fees
8.4/10 Very Good! (1,428 reviews)
"Great breakfast, nice staff, nice snacks, very clean"

Reviewed on Jun 30, 2026

Embassy Suites Charleston
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
$87 nightly
The price is $98 total per night from Jul 19 to Jul 20
$98 total
Jul 19 - Jul 20
Total with taxes and fees
8/10 Very Good! (1,000 reviews)
"Location is nice I just wish they would beautify the area . The view is of the old mall and the balcony doesn’t open . My room was 63 degrees all night and I was freezing . You can not turn the heat on and fix the issue either cause it’s a boiler system . This is the second time it happened but I ..."

Reviewed on Jun 30, 2026

Charleston Marriott Town Center
See all 161 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.

Find the Best Chesapeake Vacation Packages

Chesapeake Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Yeager Airport (CRW)
Population
1,500
Top Sights
Kanawha State Forest, West Virginia State Museum and Charleston Stage Company

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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're hoping to score a cheap Chesapeake vacation package, consider traveling in December, January and February. You'll generally find lower rates on accommodations and flights during these months — perfect for budget-conscious travelers.
How many days is enough for Chesapeake?
The ideal duration for your Chesapeake vacation depends on what you'd like to see and do. Typically, a handful of days to a week will give you time to check out all the major sights and discover some hidden spots along the way.
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.
Does Expedia offer Book Now, Pay Later Chesapeake vacation packages?
Secure your perfect trip to Chesapeake with help from Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or wait for payday — we've joined forces with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans allow you to spread the total cost over 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to stay on budget and snap up bargains before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.