Chesapeake City County Vacations & Trips from $668

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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

The Latest Chesapeake City County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Atrium Resort, Virginia Beach by Vacatia
Ocean 27
Holiday Inn & Suites Virginia Beach North Beach by IHG
Boardwalk Resort and Villas
The Ocean Key Virginia Beach Resort

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

Wingate by Wyndham Chesapeake

2.5 out of 5
817 Greenbrier Circle Chesapeake VA
Fully refundableReserve now, pay when you stay
$82 nightly
The price is $96 total per night from Mar 29 to Mar 30
$96 total
Mar 29 - Mar 30
Total with taxes and fees
8/10 Very Good! (1,003 reviews)
DO NOT STAY AT THIS HOTEL! CARPET AND BATHROOM OUTSIDE HANDLE HAD RED STAINS RESEMBLING BLOOD. TV IN HOTEL DID NOT HAVE A CLEAR SIGNAL SO THERE WAS NO WATCHING TV. TELEPHONE IN ROOM WAS DIRTY. BATHROOM HAD FLOATING SHELF AND NOT FULL SINK. BED SHEETS WERE STAINED. YOU CAN HEAR OTHER GUESTS' CONVERSATIONS ...

Reviewed on Mar 16, 2026

Wingate by Wyndham Chesapeake
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

3 out of 5
1801 Atlantic Ave Virginia Beach VA
Fully refundable
$105 nightly
The price is $123 total per night from Mar 22 to Mar 23
$123 total
Mar 22 - Mar 23
Total with taxes and fees
8.4/10 Very Good! (2,504 reviews)
We had one overnight and Country Inn & Suites was perfect. Check-in was fast & easy. The staff were friendly and helpful. The hallways were clean, the elevator worked well, the room was clean. The ocean front view was perfect. The room was clean, the bathroom was clean, the bed was comfortable, the ...

Reviewed on Mar 19, 2026

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

3 out of 5
1101 Atlantic Ave Virginia Beach VA
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $109 total per night from Apr 12 to Apr 13
$109 total
Apr 12 - Apr 13
Total with taxes and fees
8.4/10 Very Good! (1,218 reviews)
My only ding was the parking. 13 spaces at the hotel, FCFS, otherwise park a short half block away. If you have any walking difficulties, might find this not ideal. Staff, room, great.

Reviewed on Mar 20, 2026

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.