Chesapeake Vacations from $574

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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.

The Latest Chesapeake vacation packages

Price found within the past 48 hours. Click for updated prices.
Studio 6 Suites Hurricane, Wv

Studio 6 Suites Hurricane, Wv

2 out of 5
Price was $623, price is now $574 per person
$574
per person
Jan 5 - Jan 8
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Charleston (CRW)
6.4/10 (11 reviews)
Nothing wrong with an old building, but some maintenance is necessary.

Reviewed on Aug 6, 2026

Holiday Inn Express Hotel & Suites Cross Lanes by IHG

Holiday Inn Express Hotel & Suites Cross Lanes by IHG

2.5 out of 5
Price was $603, price is now $600 per person
$600
per person
Jan 5 - Jan 8
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Charleston (CRW)
9/10 Wonderful! (1,001 reviews)
great place to stay. staff was very good.

Reviewed on Nov 11, 2026

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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
$99 nightly
The price is $112 total per night from Dec 14 to Dec 15
$112 total
Dec 14 - Dec 15
Total with taxes and fees
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
$106 nightly
The price is $120 total per night from Nov 22 to Nov 23
$120 total
Nov 22 - Nov 23
Total with taxes and fees
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 Nov 22 to Nov 23
$98 total
Nov 22 - Nov 23
Total with taxes and fees
Charleston Marriott Town Center
See all 159 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 from $574 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.