Chesapeake City County Holidays
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Top hotels in Chesapeake City County
Hilton Vacation Club Ocean Beach Club Virginia Beach
3401 Atlantic Ave Virginia Beach VA
Fully refundableReserve now, pay when you stay
Rp1.272.619
Rp2.013.906 total
18 Oct - 19 Oct
includes taxes & fees
8.4/10 Very good! (1,591 reviews)
"Perfect location for MOCA Boardwalk Art Festival!! Very convenient. My only complaint was I didn’t like the two doors for the suites - traveling alone that made me feel somewhat uncomfortable. Also the doors slam very loudly - and my schedule verses the person sharing the doors was very opposite. ..."
Reviewed on 11 Oct 2026
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel
1101 Atlantic Ave Virginia Beach VA
Fully refundable
Rp1.433.710
Rp1.684.564 total
18 Oct - 19 Oct
includes taxes & fees
8.2/10 Very good! (1,620 reviews)
"The staff is wonderful. Friendly, helpful and engaged"
Reviewed on 12 Oct 2026
Hilton Vacation Club Oceanaire Virginia Beach
3421 Atlantic Ave Virginia Beach VA
Fully refundableReserve now, pay when you stay
Rp1.430.130
Rp2.195.043 total
13 Oct - 14 Oct
includes taxes & fees
8.2/10 Very good! (1,253 reviews)
"The staff was kind and welcoming and the beach view was nice."
Reviewed on 11 Oct 2026
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 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
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 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.
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 cafes.
What to do in Chesapeake City County
Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin
Rp766.070
per adult
80% of travellers recommend
City Cruises Norfolk: Signature Dinner Cruise
Rp1.541.123
per adult
76% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
