Chesapeake City County Vacation Packages
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Your Chesapeake City County Vacation
Leave the planning to us with a Chesapeake City County vacation package. With everything organized 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 customized Chesapeake City County vacation today.
Top Chesapeake City County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Blackbeard's Lodge
CA $1,341
per person
Oct 18 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
8.4/10 Very good! (384 reviews)
Blackbeard's is an older hotel very conveniently located on the island. maintenance lacks. Ice maker broken, faucets are loose etc. The staff, Cynthia, was very helpful and responsive.
Reviewed on Aug 23, 2026
Pony Island Inn
CA $1,423
per person
Oct 18 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
9.4/10 Exceptional! (489 reviews)
This is a very charming spot to power down from a day filled with Ocrakokean fun.
Perfectly located. Extremely friendly staff.
Reviewed on Aug 24, 2026
Chesapeake City County Hotel Deals
Wyndham Virginia Beach Oceanfront
5700 Atlantic Ave Virginia Beach VA
Fully refundableReserve now, pay when you stay
CA $131
CA $164 total
Aug 31 - Sep 1
includes taxes & fees
7.8/10 Good! (2,025 reviews)
"Everyone was very nice and welcoming, next year we’ll be staying here again for sure!"
Reviewed on Aug 24, 2026
Ocean Resort
Atlantic Avenue,2417 Virginia Beach VA
Fully refundableReserve now, pay when you stay
CA $109
CA $147 total
Sep 23 - Sep 24
includes taxes & fees
7.8/10 Good! (1,723 reviews)
"steps from beach, across from pizza, walgreens"
Reviewed on Aug 24, 2026
Crowne Plaza Virginia Beach Town Center by IHG
4453 Bonney Rd Virginia Beach VA
Fully refundable
CA $128
CA $150 total
Sep 7 - Sep 8
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 vacation package cost?
Perhaps less than you might think — from just CA $1,016, 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.
Stay near popular Chesapeake City County attractions
Greenbrier Mall
8.4/10 (837 reviews)
You can browse for the perfect souvenirs 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 find the perfect gifts to bring home at Chesapeake Square Mall during your trip to Chesapeake. Discover the top-notch restaurants and acclaimed theater 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 theater 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 theater 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 family-friendly area, or check out 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 great live music or attend a sporting event.
Chesapeake Arboretum
7.6/10 (76 reviews)
Enjoy an outing to Chesapeake Arboretum during your stay in Chesapeake. Amble around the area's beautiful beaches or attend a sporting event.
Dismal Swamp Canal
Dismal Swamp Canal is just one of the places to see in Chesapeake, so why not enjoy the other things to explore during your travels? While in this family-friendly area, you can enjoy the coffeehouses.
What to do in Chesapeake City County
City Cruises Norfolk: Signature Dinner Cruise
CA $158
per adult
76% of travellers recommend
Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin
CA $60
per adult
100% of travellers recommend
City Cruises Norfolk: Signature Brunch Cruise
CA $136
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
