Chesapeake City County Holidays

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Top destinations in Chesapeake City County

Colorful sunset over riverside resort in Cambridge Maryland USA
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Chesapeake

Top hotels in Chesapeake City County

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 3.157.200 ₫ per night from 28 Jun to 29 Jun
3.157.200 ₫
3.683.400 ₫ total
28 Jun - 29 Jun
includes taxes & fees
7.8/10 Good! (1,078 reviews)
"The Wi-Fi connection is terrible it would not hold a connection for longer than about 10 minutes and then would disconnect. The hot water is non-existent on the third floor - I let it run for more than 15 minutes and it still was barely lukewarm. The room was clean, but the hallways are dark and ..."

Reviewed on 14 Jun 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 3.007.233 ₫ per night from 15 Jun to 16 Jun
3.007.233 ₫
3.706.158 ₫ total
15 Jun - 16 Jun
includes taxes & fees
7.8/10 Good! (1,872 reviews)
"I have stayed at Wyndham properties before, including locations in Dallas and Las Vegas. Unfortunately, this property was poorly maintained throughout. From the moment I entered the lobby, it was apparent that the facility was not being properly cared for. The furniture was stained, scratched, and ..."

Reviewed on 13 Jun 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 7.971.930 ₫ per night from 15 Jun to 16 Jun
7.971.930 ₫
9.220.340 ₫ total
15 Jun - 16 Jun
includes taxes & fees
9.4/10 Exceptional! (2,325 reviews)
"We very much enjoyed our stay. Easy access to beach. Clean rooms, property well maintained. Tamara and Ty at breakfast were so accommodating at replenishing food. Just a suggestion. Just a suggestion perhaps posting a sign letting guests know to pick up after themselves. Again overall a fantastic ..."

Reviewed on 13 Jun 2026

Hyatt Place Virginia Beach / Oceanfront
See all 3,457 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 1null000null000 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 rentals 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.

Stay near popular Chesapeake City County attractions

Greenbrier Mall

4.2/5 (837 reviews)
You can search for that perfect souvenir 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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