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.

Chesapeake

Chesapeake

Chesapeake City County Hotel Deals

Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

5700 Atlantic Ave Virginia Beach VA
Fully refundableReserve now, pay when you stay
NT$3,033
NT$3,788 total
Aug 31 - Sep 1
includes taxes & fees
7.8/10 Good! (2,019 reviews)
"Property is older but my room was clean and my stay was pleasant"

Reviewed on 2026/8/23

Wyndham Virginia Beach Oceanfront
Ocean Resort

Ocean Resort

Atlantic Avenue,2417 Virginia Beach VA
Fully refundableReserve now, pay when you stay
NT$2,697
NT$3,605 total
Sep 20 - Sep 21
includes taxes & fees
7.8/10 Good! (1,711 reviews)
"Staff was very helpful and courteous was very accommodating. I ended up extending my stay and they were very helpful and helping me with the extension and giving me a separate room."

Reviewed on 2026/8/22

Ocean Resort
Crowne Plaza Virginia Beach Town Center by IHG

Crowne Plaza Virginia Beach Town Center by IHG

4453 Bonney Rd Virginia Beach VA
Fully refundable
NT$2,963
NT$3,471 total
Sep 7 - Sep 8
includes taxes & fees
Crowne Plaza Virginia Beach Town Center by IHG
See all 3,482 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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A building with a clock tower, surrounded by pink flowers and greenery.

Chesapeake Square Mall

8.2/10 (429 reviews)
You can find the perfect gifts to bring home at Chesapeake Square Mall during your trip to Chesapeake. Discover the top-notch restaurants and acclaimed theater scene in this family-friendly area.
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A modern building with a curved glass facade and a sign reading "Chesapeake Conference Center."

Chesapeake Conference Center

7.8/10 (169 reviews)
After visiting Chesapeake Conference Center, make a plan to see the other sights and activities in Chesapeake. Experience the area's great live music and acclaimed theater scene.
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A wooden bridge over a calm river surrounded by dense forest.

Chesapeake City Park

8.2/10 (180 reviews)
Chesapeake City Park is just one of the places to see in Chesapeake, so why not enjoy the other things to explore during your travels? Stroll along the area's beautiful beaches or experience its acclaimed theater scene.
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A solitary tree in a swampy area with water around its base.

Lake Drummond

7.8/10 (12 reviews)
Commune with nature and explore the great outdoors at Lake Drummond during your travels in Chesapeake. Stroll along the beautiful beaches in this family-friendly area, or check out its top-notch restaurants.
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A wooden pier extending into a calm lake, surrounded by dense trees.
Photo by Kaylee Spinhirn

Oak Grove Lake Park

7.6/10 (39 reviews)
After visiting Oak Grove Lake Park, make a plan to see the other sights and activities in Chesapeake. Experience the area's great live music or attend a sporting event.
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Chesapeake Arboretum

7.6/10 (76 reviews)
Enjoy an outing to Chesapeake Arboretum during your stay in Chesapeake. Amble around the area's beautiful beaches or attend a sporting event.
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Dismal Swamp Canal

Dismal Swamp Canal is just one of the places to see in Chesapeake, so why not enjoy the other things to explore during your travels? While in this family-friendly area, you can enjoy the coffeehouses.
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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.