Chesapeake City County Vacations & Trips

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NT$5,067 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top destinations in Chesapeake City County

Chesapeake Square Mall
FlightsFlightsHotelsHotels

Chesapeake

Chesapeake

Chesapeake City County Hotel Deals

Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake

2.5 out of 5
817 Greenbrier Circle Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is NT$2,467 per night from Nov 23 to Nov 24
NT$2,467
NT$2,899 total
Nov 23 - Nov 24
includes taxes & fees
8/10 Very Good! (1,002 reviews)
Great

Reviewed on 2025/11/6

Wingate by Wyndham Chesapeake
Schooner Inn

Schooner Inn

2 out of 5
215 Atlantic Ave Virginia Beach VA
The price is NT$2,179 per night from Nov 23 to Nov 24
NT$2,179
NT$2,568 total
Nov 23 - Nov 24
includes taxes & fees
8.6/10 Excellent! (3,632 reviews)
Loved this little inn, would love to gate-keep it forever! It was soo nice to be able to go up to the boardwalk if we wanted, but we did not really need to since the Beachfront was so nice and calm on that end as well. Clean. So clean. Loved the breezeway. Did not expect the small efficiency kitchen, ...

Reviewed on 2025/11/13

Schooner Inn
Hyatt Place Virginia Beach Town Center

Hyatt Place Virginia Beach Town Center

3 out of 5
335 Independence Blvd Virginia Beach VA
Fully refundableReserve now, pay when you stay
The price is NT$4,329 per night from Nov 17 to Nov 18
NT$4,329
NT$5,041 total
Nov 17 - Nov 18
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
The room was clean and exactly what we were looking for.

Reviewed on 2025/11/13

Hyatt Place Virginia Beach Town Center
See all 3,427 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.