Chesapeake City County Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Our pick of the best Chesapeake City County Hotel Deals
Comfort Suites Chesapeake - Norfolk
1550 Crossways Blvd Chesapeake VA
Fully refundable
NZ$174
22 Nov - 23 Nov
includes taxes & fees
9/10 Wonderful! (1,139 reviews)
"Everyone was pleasant. The facility was clean."
Reviewed on 22 Oct 2026
YourSpace Hotels Chesapeake
2137 Starmount Parkway Chesapeake VA
NZ$177
29 Oct - 30 Oct
includes taxes & fees
9.6/10 Exceptional! (257 reviews)
"It was very clean and the staff was super friendly."
Reviewed on 22 Oct 2026
Hilton Vacation Club Ocean Beach Club Virginia Beach
3401 Atlantic Ave Virginia Beach VA
Fully refundableReserve now, pay when you stay
NZ$190
25 Oct - 26 Oct
includes taxes & fees
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.
Stay near popular Chesapeake City County attractions
Greenbrier Mall
8.4/10 (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.
Chesapeake Square Mall
8.2/10 (429 reviews)
You can search for that perfect souvenir at Chesapeake Square Mall during your visit to Chesapeake. Discover the top-notch restaurants and acclaimed theatre scene in this family-friendly area.
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 theatre scene.
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 theatre scene.
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 romantic area or visit its top-notch restaurants.
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 acclaimed theatre scene or attend a sporting event.
Chesapeake Golf Club
7.4/10 (93 reviews)
Enjoy a round of golf in Chesapeake at Chesapeake Golf Club. Experience the great live music or attend a sporting event in this family-friendly area.
Chesapeake Veterans' Memorial
8.0/10 (79 reviews)
Learn about the local history of Chesapeake when you take a trip to Chesapeake Veterans' Memorial. Stroll along the area's beautiful beaches or experience its great live music.
What to do in Chesapeake City County
Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin
NZ$75
per adult
80% of travellers recommend
Buried Beneath the Boardwalk: Neptune Ghouls and Ghost Tours
NZ$42
per adult
Ziplining and Climbing at The Adventure Park at Virginia Aquarium
NZ$107
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
