
Chesapeake City County Vacations & Trips from $624
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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.


Sea Ranch Resort
Price was $3,239, price is now $2,120 per person
$2,120
per person
Apr 18 - Apr 22
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.6/10 Excellent! (1,001 reviews)
The room was clean, spacious, and comfortable. Privacy was respected. However, I couldn’t change the thermostat temperature lower (I guess it was locked because it was winter) as I get hot easily. The pool was nice and I liked that it was heated, but there were no towels on the racks. I wish there were showers in the pool area. I couldn’t get in the fitness center initially as the lock was broken. I did not eat at the restaurant.
Reviewed on Jan 30, 2026

Ocean 27
Northeast Virginia Beach
Save 100% on your flight
Price was $2,458, price is now $1,748 per person
$1,748
per person
Mar 6 - Mar 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
6.4/10 (1,090 reviews)
Close to beach. Ground level beach access rooms. Grounds need to be picked-up a bit. Centrally located along boardwalk.
Reviewed on Oct 13, 2025


The Sanderling
Price was $945, price is now $679 per person
$679
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Norfolk (ORF)
8.8/10 Excellent! (523 reviews)
The elevator was broken. We were told that had been struck by lightning. I was also told that it had been broken for one year. They have three floors almost 2 of the buildings and I think two on the other, but I don’t know if they meant elevators in the building that we were in or every single one wasn’t clarified also told that they were having a New Year’s Eve celebration. Nothing was held in the lobby as previously expected the restaurant on site closed at 9 PM New Year’s Eve and we were rushed like you wouldn’t believe for six course meal that cost $300.
Reviewed on Jan 7, 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

Wingate by Wyndham Chesapeake
817 Greenbrier Circle Chesapeake VA
$75 nightly
The price is $88 total per night from Feb 15 to Feb 16
$88 total
Feb 15 - Feb 16
Total with taxes and fees
7.8/10 Good! (1,000 reviews)
Great customer service
Reviewed on Feb 2, 2026

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)
1801 Atlantic Ave Virginia Beach VA
$95 nightly
The price is $111 total per night from Feb 11 to Feb 12
$111 total
Feb 11 - Feb 12
Total with taxes and fees
8.2/10 Very Good! (2,489 reviews)
all around well done
Reviewed on Jan 28, 2026

Holiday Inn Va Beach-Oceanside (21st St) by IHG
2101 Atlantic Avenue Virginia Beach VA
Fully refundable
$134 nightly
The price is $156 total per night from Feb 18 to Feb 19
$156 total
Feb 18 - Feb 19
Total with taxes and fees
8.8/10 Excellent! (1,003 reviews)
Nice view of the beach
Reviewed on Jan 19, 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.
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