Chesapeake City County Vacations & Trips from $346
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 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
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.
John Yancey Oceanfront Inn
$346
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
9.2/10 Wonderful! (1,928 reviews)
Property did not disappoint. Close to all points, centered on the island. Food galore beach galore and the sunsets are unforgettable! Can’t wait to return. Property was well maintained rooms are spacious if you’re lucky to get ocean view Good Luck breathtaking sunrise.
Reviewed on Aug 30, 2026
Boardwalk Resort and Villas
Northeast Virginia Beach
$387
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8.8/10 Excellent! (1,018 reviews)
Location and Space, as well as, amenities ARE EXCELLENT!!!! WILL COME BACK❣️💯🙏
Reviewed on Aug 29, 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
Ocean Resort
Atlantic Avenue,2417 Virginia Beach VA
Fully refundableReserve now, pay when you stay
$83 nightly
$98 total
Sep 20 - Sep 21
Total with taxes and fees
Crowne Plaza Virginia Beach Town Center by IHG
4453 Bonney Rd Virginia Beach VA
Fully refundable
$91 nightly
$107 total
Sep 28 - Sep 29
Total with taxes and fees
Wyndham Virginia Beach Oceanfront
5700 Atlantic Ave Virginia Beach VA
Fully refundableReserve now, pay when you stay
$100 nightly
$117 total
Sep 20 - Sep 21
Total with taxes and fees
7.8/10 Good! (1,947 reviews)
"Loved the room. Great bed. Beautiful view. The balcony was wonderful. The restaurant was nice but the menu is very limited. I was disappointed in the bathroom. We had a handicap accessible room. However, the bathroom was not accessible for the limited mobility guest. The bath tub was dangerous. The ..."
Reviewed on Aug 30, 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.
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
$83
per adult
76% of travellers recommend
Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin
$43
per adult
80% of travellers recommend
City Cruises Norfolk: Signature Brunch Cruise
$79
per adult
88% of travellers recommend
Explore a world of travel with Expedia
Other vacations you might like
- Top cities in Chesapeake City County
- Vacations and getaways similar to Chesapeake City County
- Best vacation destinations by month
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
