Chesapeake City County Vacations & Trips from $193
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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 destinations in Chesapeake City County
Chesapeake
The Latest Chesapeake City County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Boardwalk Resort and Villas
Northeast Virginia Beach
$220
per person
Nov 6 - Nov 8
found 9 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Norfolk (ORF)
8.8/10 Excellent! (1,006 reviews)
We loved that we had a balcony and also the living room windows were the whole length and width of the room. Great for looking out. I had email staff to see about
getting a room on 5th or 6th floor. They were very nice and said they could not
guarantee, but they would try their best. They ended up getting us on the 6th floor.
We were amazed also, how fast the elevators were. Some that we have stayed was very, very slow at other hotels. Also, the lights of the hotel that lite up the beach were great for people that wanted to set out on the beach after dark.
Reviewed on Sep 22, 2026
Find the Best Chesapeake City County Vacation Packages
Chesapeake City County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Norfolk Intl. Airport (ORF) |
Top Sights | Chesapeake City Park, Oak Grove Lake Park and Lake Drummond |
Chesapeake City County Hotel Deals
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)
1801 Atlantic Ave Virginia Beach VA
Fully refundable
$113 nightly
$132 total
Sep 27 - Sep 28
Total with taxes and fees
8.6/10 Excellent! (2,796 reviews)
"Add some fresh fruits! The foods are so dry.."
Reviewed on Sep 23, 2026
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel
1101 Atlantic Ave Virginia Beach VA
Fully refundable
$76 nightly
$89 total
Oct 21 - Oct 22
Total with taxes and fees
8.4/10 Very Good! (1,589 reviews)
"Room was spacious and comfortable. Balcony ocean view was perfect. Parking was atrocious. Only a dozen spots with only 2 handicapped spots. Otherwise it was a 2 block walk to park in a reserved lot. No breakfast available but bar attached had really good food and bar servers were great. Very convenient ..."
Reviewed on Sep 23, 2026
Hilton Vacation Club Ocean Beach Club Virginia Beach
3401 Atlantic Ave Virginia Beach VA
Fully refundableReserve now, pay when you stay
$92 nightly
$108 total
Sep 27 - Sep 28
Total with taxes and fees
8.4/10 Very Good! (1,537 reviews)
"I love the sound of the ocean."
Reviewed on Sep 23, 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.
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.
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 theater scene or attend a sporting event.
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 check out its top-notch restaurants.
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.
Camelot Park
Camelot 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 beautiful beaches or visit the shops in this family-friendly area.
What to do in Chesapeake City County
Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin
$43
per adult
80% of travellers recommend
City Cruises Norfolk: Signature Dinner Cruise
$83
per adult
76% of travellers recommend
City Cruises Norfolk: Signature Brunch Cruise
$79
per adult
88% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
