Chesapeake City County Vacations & Trips from $242
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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.
Roanoke Island Inn
Historic Downtown Manteo
$525
per person
Dec 9 - Dec 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
10/10 Exceptional! (103 reviews)
Staff and owners were very welcoming. We accidentally left a few items, which they offered to mail to us. Our kids loved the koi pond.
Reviewed on Oct 11, 2026
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Northeast Virginia Beach
$636
per person
Dec 16 - Dec 20
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.2/10 Very Good! (1,425 reviews)
Front desk ladies were super nice. And the maintenance staff were welcoming throughout the weekend. Great hotel 5/5 recommend for the price!
Reviewed on Oct 15, 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
Comfort Suites Chesapeake - Norfolk
1550 Crossways Blvd Chesapeake VA
Fully refundable
$83 nightly
$98 total
Nov 15 - Nov 16
Total with taxes and fees
Hilton Vacation Club Ocean Beach Club Virginia Beach
3401 Atlantic Ave Virginia Beach VA
Fully refundableReserve now, pay when you stay
$96 nightly
$113 total
Oct 22 - Oct 23
Total with taxes and fees
8.4/10 Very Good! (1,601 reviews)
"First time here but will definitely back. Very family friendly place, staff are very friendly and helpful.Recommend it for everyone. Pool’s are great and the kids love them. Rooms are great quiet and very clean and comfortable ."
Reviewed on Oct 15, 2026
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel
1101 Atlantic Ave Virginia Beach VA
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.
Chesapeake Veterans' Memorial
8.0/10 (79 reviews)
Learn about the local history of Chesapeake with a stop at Chesapeake Veterans' Memorial. Stroll along the area's beautiful beaches or experience its great live music.
Chesapeake Golf Club
7.4/10 (93 reviews)
Enjoy a round of golf in Chesapeake at Chesapeake Golf Club. Experience the great live music or attend a sporting event 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
$93
per adult
76% of travellers recommend
Ziplining and Climbing at The Adventure Park at Virginia Aquarium
$64
per adult
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