Chesapeake City County Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Kaylee Spinhirn

  • Plan, book, travel with confidence

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    Better together

    Save up to NZ$616 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Our pick of the best Chesapeake City County Hotel Deals

Surfbreak Virginia Beach Oceanfront, Ascend Hotel Collection

Surfbreak Virginia Beach Oceanfront, Ascend Hotel Collection

3 out of 5
1101 Atlantic Ave, Virginia Beach, VA
Fully refundableReserve now, pay when you stay
The price is NZ$200 per night from 14 Sept to 15 Sept
NZ$200
14 Sept - 15 Sept
includes taxes & fees
8.2/10 Very Good! (1,071 reviews)
"Muy limpio y las personas muy amables"

Reviewed on 14 Aug. 2025

Surfbreak Virginia Beach Oceanfront, Ascend Hotel Collection
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 NZ$192 per night from 1 Sept to 2 Sept
NZ$192
1 Sept - 2 Sept
includes taxes & fees
7.6/10 Good! (1,615 reviews)
"Pool, bar, music, food, location"

Reviewed on 13 Aug. 2025

Wyndham Virginia Beach Oceanfront
Oceans 2700

Oceans 2700

2.5 out of 5
2700 Pacific Avenue, Virginia Beach, VA
Fully refundableReserve now, pay when you stay
8/10 Very Good! (1,368 reviews)
"Great location"

Reviewed on 13 Aug. 2025

Get rates
Oceans 2700
See all 3,428 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 holiday 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 holiday package. It's as easy as that! From flights and hotels to activities and rental cars, Expedia makes travelling 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 holiday?
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 holiday homes such as beach villas and city residences. The list is almost endless!
Can I choose my airline with a Chesapeake City County Expedia holiday 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 holiday package?
If your holiday 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.