Chesapeake City County Vacations & Trips

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Top destinations in Chesapeake City County

A golf course, a large building complex, and a marina by a river.
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Chesapeake

Chesapeake

Chesapeake City County Hotel Deals

Hyatt Studios Chesapeake

Hyatt Studios Chesapeake

2 out of 5
101 Volvo Parkway Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is NT$5,113 per night from Jul 15 to Jul 16
NT$5,113
NT$5,945 total
Jul 15 - Jul 16
includes taxes & fees
7.8/10 Good! (24 reviews)
"Check in July 2nd and Departed July 6th newer hotel everything was still fairly new spotless up to date dishwasher refrigerator stove top electric and microwave oven good size flat screen television and comfortable bed and couch nice clean also bed couch at that walk in shower space decent I am glad ..."

Reviewed on 2026/7/8

Hyatt Studios Chesapeake
Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake

3 out of 5
817 Greenbrier Circle Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is NT$3,949 per night from Aug 9 to Aug 10
NT$3,949
NT$4,606 total
Aug 9 - Aug 10
includes taxes & fees
7.8/10 Good! (1,110 reviews)
"The room was very nice, roomy and comfortable."

Reviewed on 2026/7/7

Wingate by Wyndham Chesapeake
Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

3 out of 5
5700 Atlantic Ave Virginia Beach VA
Fully refundableReserve now, pay when you stay
The price is NT$4,845 per night from Jul 23 to Jul 24
NT$4,845
NT$5,874 total
Jul 23 - Jul 24
includes taxes & fees
7.8/10 Good! (1,879 reviews)
"Terrible staff"

Reviewed on 2026/7/8

Wyndham Virginia Beach Oceanfront
See all 3,436 properties in Chesapeake City County
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.

Frequently asked questions

How much does a Chesapeake City County vacation package cost?
Perhaps less than you might think — from just , actually! By bundling hotels, flights and car rentals into a custom-built package, your getaway to Chesapeake City County is just clicks away.
How do I get a cheap travel package to Chesapeake City County?
Find flights that suit your schedule, add a hotel to your booking and watch the savings rack up with a Chesapeake City County vacation package. It's as easy as that! From flights and hotels to activities and rental cars, Expedia makes traveling on a budget easy. And with over 550 partner airlines and 1,000,000 properties globally to choose from, you'll never be short of choice.
What are the top hotels in Chesapeake City County?
Hyatt Place Chesapeake and Aloft Chesapeake are a couple of welcoming options in Chesapeake. A key stop on any good Chesapeake City County itinerary, we recommend taking the time to really explore this impressive city.
How far in advance should I book my Chesapeake City County vacation?
Search Expedia to compare international airfares as soon as you've got your travel dates. You can normally purchase a seat up to 12 months before departure. If you can't see your preferred air carrier, or you've left things to the last moment, fear not. Cheap tickets to Chesapeake City County occasionally appear within weeks of departure.
What does an Expedia Chesapeake City County travel package include?
You can choose from any combination of rental cars, hotels and flights. Once you've made your booking, you can add activities and experiences. Want to pick your fare class? That's also possible. The choice is all yours when it comes to putting together your dream Chesapeake City County getaway.
What should I know before booking a Chesapeake City County travel package?
Booking all the parts of your escape together is a smart way to save. Combine your car rentals, flights and hotels into a handy little package. But you're not limited to hotels. Expedia offers all sorts of properties, including vacation rentals such as beach villas and city residences. The list is almost endless!
Can I choose my airline with a Chesapeake City County Expedia vacation package?
Expedia offers access to more than 550 airline partners globally, so you sure can! Just select your preferred carrier and craft your ideal Chesapeake City County trip.
If I'm not able to travel, can I cancel my Chesapeake City County vacation package?
If your vacation plans in Chesapeake City County have changed, it's a relief to know that it is possible to cancel your booking. If you booked in the last 24 hours, you may be eligible to receive a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may impose a cancellation fee. For more details, check our Customer Service Portal.

Stay near popular Chesapeake City County attractions

A CVS store with a large archway and a red star logo.

Greenbrier Mall

8.4/10 (837 reviews)
You can browse for the perfect souvenirs at Greenbrier Mall during your visit to Chesapeake. Stroll along the beautiful beaches or attend a sporting event in the 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.