Chesapeake Vacations from $468

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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.
Wyndham Garden Cross Lanes Charleston

Wyndham Garden Cross Lanes Charleston

2.5 out of 5
Price was $532, price is now $468 per person
$468
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Charleston (CRW)
7/10 Good! (1,000 reviews)
Needs a renovation.

Reviewed on Apr 10, 2026

Hampton Inn Charleston-Southridge

Hampton Inn Charleston-Southridge

2.5 out of 5
Ruthdale
Price was $1,323, price is now $1,054 per person
$1,054
per person
Jun 15 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Charleston (CRW)
9.4/10 Exceptional! (1,003 reviews)
Clean room and breakfast

Reviewed on May 6, 2026

Opossum Creek Retreat

Opossum Creek Retreat

3 out of 5
Price was $969, price is now $775 per person
$775
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Charleston (CRW)
9.4/10 Exceptional! (53 reviews)
Perfect, perfect, perfect!

Reviewed on Apr 7, 2026

Courtyard by Marriott Charleston Downtown/Civic Center

Courtyard by Marriott Charleston Downtown/Civic Center

3 out of 5
Downtown Charleston
Price was $1,294, price is now $1,128 per person
$1,128
per person
Jun 15 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Charleston (CRW)
9/10 Wonderful! (1,000 reviews)
The room was clean and comfortable

Reviewed on Mar 31, 2026

Holiday Inn Express Charleston-Civic Center by IHG

Holiday Inn Express Charleston-Civic Center by IHG

2.5 out of 5
Downtown Charleston
Price was $1,061, price is now $926 per person
$926
per person
Jun 15 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Charleston (CRW)
8.6/10 Excellent! (1,168 reviews)
To start I wasn’t happy about $10 to park, just seems ridiculous! The room was ok when we walked in. Got in late so went to dinner then came back and headed to bed. Went to wash my face and there was only a trickle of hot water but it wasn’t hot. Ended up washing my face in the tub because I needed HOT WATER! I paid enough for hot water. Got up and a soda cup and water cup were covered in ants. That is really not ok. Can’t wash the cup in the sink because still water pressure or heat. We were just staying one night so that helped. Told the front deck about the problem but she didn’t seem to worried, said I’ll pass it on. The breakfast was very good and filled us up before a long day of driving.

Reviewed on Apr 29, 2026

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Discover the most popular places to visit in Chesapeake

West Virginia State Capitol Building

West Virginia State Capitol Building

Take a guided tour around West Virginia’s seat of government and marvel at its dazzling dome, which is covered in 23.5-karat gold.

West Virginia State Capitol Building
showgirl in red costume

Mardi Gras Casino

Why not roll the dice with a visit to Mardi Gras Casino during your time in Cross Lanes? Wander the area's riverfront or simply enjoy one of its top-notch restaurants.

Mardi Gras Casino
Aerial Elevating Up Over Chruch Clocktower and Charleston West Virginia

Charleston Town Center

You can search for that perfect souvenir at Charleston Town Center during your visit to Charleston. While in this walkable area, find time to visit its casinos.

Charleston Town Center

Chesapeake Hotel Deals

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 May 17 to May 18
$98 total
May 17 - May 18
Total with taxes and fees
8/10 Very Good! (1,009 reviews)
Breakfast was good.

Reviewed on May 7, 2026

Charleston Marriott Town Center
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 May 17 to May 18
$138 total
May 17 - May 18
Total with taxes and fees
8.4/10 Very Good! (1,381 reviews)
We paid for a corner room with two queen beds and a sofa roll away bed. When we got to the hotel, the person at the front desk did not provide us with the room we paid for. She was rude and deflecting... An elevator did not work and the stairs could only be accessed from outside the property... There ...

Reviewed on May 4, 2026

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
$101 nightly
The price is $114 total per night from May 17 to May 18
$114 total
May 17 - May 18
Total with taxes and fees
8.6/10 Excellent! (1,169 reviews)
Breakfast was the best of all the Holiday Inns we stayed in the last 4 days. Good tasting and room was clean. Give the hostess a bonus. Placed in room 100, next to lobby. Not good. Could hear late guests arriving. Also, did not appreciate the 0530 wake up call which I did not ask for.

Reviewed on May 4, 2026

Holiday Inn Express Charleston-Civic Center by IHG
See all 166 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 $468 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.