Chesapeake City County Vacations & Trips from $261
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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.
Comfort Suites Airport
Central Newport News
$261
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8.8/10 Excellent! (1,125 reviews)
My stay was absolutely divine. I appreciate the immediate hospitable service when my family and I arrived. I loved how clean the room and main lobby were. And the furniture was extremely comfortable! 10 out of 10. Thank you for a pleasant and memorable experience.
Reviewed on Sep 11, 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
Wyndham Virginia Beach Oceanfront
5700 Atlantic Ave Virginia Beach VA
Fully refundableReserve now, pay when you stay
$94 nightly
$110 total
Oct 4 - Oct 5
Total with taxes and fees
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)
1801 Atlantic Ave Virginia Beach VA
Fully refundable
$116 nightly
$137 total
Oct 6 - Oct 7
Total with taxes and fees
8.6/10 Excellent! (2,765 reviews)
"The room was clean and the ocean view was beautiful. This is a family friendly hotel."
Reviewed on Sep 10, 2026
Holiday Inn & Suites Virginia Beach North Beach by IHG
3900 Atlantic Avenue Virginia Beach VA
Fully refundable
$127 nightly
$148 total
Oct 11 - Oct 12
Total with taxes and fees
8/10 Very Good! (1,535 reviews)
"We love this property because it’s prime location. On the quiet end of the beach very convenient. The shuttle is right outside as is 7/11 and the rest is within a few block walk. The pools here are the best we spend our days hopping from one pool to the beach to another’s it’s nice they have a kids ..."
Reviewed on Sep 11, 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 romantic 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 acclaimed theater scene 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.
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.
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
Buried Beneath the Boardwalk: Neptune Ghouls and Ghost Tours
$24
per adult
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