Chesapeake Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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
Embassy Suites Charleston
300 Court St Charleston WV
Fully refundableReserve now, pay when you stay
The price is CA $180 per night from Jun 9 to Jun 10
CA $180
CA $203 total
Jun 9 - Jun 10
includes taxes & fees
8.4/10 Very Good! (1,406 reviews)
"The front desk could use a sign. It's on the right from the front door. It looks a lot like the bar that's on the left."
Reviewed on May 25, 2026
Charleston Marriott Town Center
200 Lee St E Charleston WV
Fully refundableReserve now, pay when you stay
The price is CA $142 per night from Jun 9 to Jun 10
CA $142
CA $161 total
Jun 9 - Jun 10
includes taxes & fees
8.2/10 Very Good! (1,008 reviews)
"We felt rather sad staying here. The property is rather dated. Not exactly run down, but definitely worn. The chip out of our sink, the buckling carpet that needs to be restretched (or replaced)...there were a number of little things that prevent me from giving my endorsement."
Reviewed on May 22, 2026
Holiday Inn Express Charleston-Civic Center by IHG
100 Civic Center Drive Charleston WV
Fully refundable
The price is CA $139 per night from Jun 7 to Jun 8
CA $139
CA $158 total
Jun 7 - Jun 8
includes taxes & fees
8.6/10 Excellent! (1,166 reviews)
"Clean room and good breakfast- props to the employee that was keeping all the breakfast food coming. Appreciated the handout of places that would deliver- and the 24/7 coffee/tea/water service. The work out area and lobby were well kept"
Reviewed on May 25, 2026
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
Southridge Center
4.5/5(4 reviews)
You can do some window-shopping at Southridge Center during your stay in Charleston. Stroll along the riverfront or visit the casinos in this relaxing area.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
