Chesapeake City County Holidays

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Your Chesapeake City County Holiday

Leave the planning to us with a Chesapeake City County holiday package. With everything organised before you leave home, the only thing left for you to do is relax and experience this destination's beauty and culture. Not sure where your first stop should be? Chesapeake is among the most popular cities to visit during a trip to Chesapeake City County. Expedia has hotels, flights and all your other travel needs to help you put together your very own customised Chesapeake City County holiday today.

Top destinations in Chesapeake City County

Colorful sunset over riverside resort in Cambridge Maryland USA
FlightsFlightsHotelsHotels

Chesapeake

Chesapeake

Chesapeake City County Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Norfolk Intl. Airport (ORF)
Top Sights
Chesapeake City Park, Lake Drummond and Oak Grove Lake Park

Our pick of the best Chesapeake City County Hotel Deals

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 AU$177 per night from 1 June to 2 June
AU$177
1 June - 2 June
includes taxes & fees
8/10 Very Good! (1,051 reviews)
"The hotel was clean, but older and not updated. The Jacuzzi in the pool area was not functional, and the outlet in my bathroom was not functioning so no use of hairdryer or other electric small appliances. Of the three Wyndham properties I stayed in on my travels, this was the most expensive but ..."

Reviewed on 24 May 2026

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 AU$169 per night from 27 May to 28 May
AU$169
27 May - 28 May
includes taxes & fees
7.8/10 Good! (1,829 reviews)
"Stayed in the Jr. Executive Suite and loved the additional space the room offered. There are few photos but the 2nd floor suite (there are only 2 but the 2nd floor is the one I stayed in) has 2 separate balconies, ocean view, party over patio area, view is basically dead center of hotel with panoramic ..."

Reviewed on 24 May 2026

Wyndham Virginia Beach Oceanfront
Hyatt Place Virginia Beach / Oceanfront

Hyatt Place Virginia Beach / Oceanfront

3 out of 5
3601 ATLANTIC AVENUE Virginia Beach VA
Fully refundableReserve now, pay when you stay
The price is AU$324 per night from 31 May to 1 June
AU$324
31 May - 1 June
includes taxes & fees
9.4/10 Exceptional! (2,282 reviews)
"It was perfect , clean and beautifull"

Reviewed on 23 May 2026

Hyatt Place Virginia Beach / Oceanfront
See all 3,479 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.
All Inclusive Holidays
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beach holidays
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Beach Holidays

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.