Chesapeake Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 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
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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
100 Civic Center Drive Charleston WV
Fully refundable
The price is CA $137 per night from Feb 22 to Feb 23
CA $137
CA $155 total
Feb 22 - Feb 23
includes taxes & fees
8.6/10 Excellent! (1,170 reviews)
Yes and yes
Reviewed on Feb 11, 2026
Embassy Suites Charleston
300 Court St Charleston WV
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from Mar 8 to Mar 9
CA $161
CA $182 total
Mar 8 - Mar 9
includes taxes & fees
8.2/10 Very Good! (1,326 reviews)
Everything was great other than the AC did not work at all
Reviewed on Feb 8, 2026
Charleston Marriott Town Center
200 Lee St E Charleston WV
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Feb 22 to Feb 23
CA $150
CA $169 total
Feb 22 - Feb 23
includes taxes & fees
8/10 Very Good! (1,001 reviews)
Check in was quick and easy and the staff were very friendly. Parking was quick and easy as they have a parking garage right next to the main entrance. We paid for the breakfast which wasn’t very good but we also did not pay very much for it. The room was pretty basic but it was clean and the bed ...
Reviewed on Feb 10, 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
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
