Chesapeake City County Vacations & Trips from $524
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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.
John Yancey Oceanfront Inn
Price was $717, price is now $524 per person
$524
per person
Apr 23 - Apr 28
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
9/10 Wonderful! (1,868 reviews)
Ocean view is stunning. I loved going to sleep and waking up to the sight and sound of the ocean. Great local places open close by- even in March!
Reviewed on Mar 21, 2026
Pamlico Station Edgecamp
South Rodanthe
Save 100% on your flight
Price was $1,131, price is now $803 per person
$803
per person
May 27 - May 31
just found
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
9.4/10 Exceptional! (24 reviews)
This hotel was fabulous. Staff were super friendly and made pre-check in so easy, and were very quick to respond to any questions. Everything was so clean, thoughtful, and welcoming. Amenities were amazing, relaxing and clean. Kitchen was fully equipped with everything you need and very clean.
Reviewed on Mar 18, 2026
The Sanderling
Save 100% on your flight
Price was $2,709, price is now $1,948 per person
$1,948
per person
Jun 4 - Jun 11
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.8/10 Excellent! (529 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
The Burrus House Inn Waterfront Suites
Save 100% on your flight
Price was $1,183, price is now $851 per person
$851
per person
May 27 - May 31
just found
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
9.6/10 Exceptional! (27 reviews)
What a gorgeous property- conveniently located, close to the beaches and all types of activities. We couldn’t have been happier.
Andrew and Julie G.
Reviewed on Sep 1, 2025
Hilton Norfolk The Main
Downtown Norfolk
Save 100% on your flight
Price was $1,577, price is now $1,164 per person
$1,164
per person
Jun 4 - Jun 11
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
9/10 Wonderful! (1,011 reviews)
From the restaurants to the room and the employees. Everything was exceptional
Reviewed on Mar 20, 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
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! (1,007 reviews)
Room smelled bad but bed was comfortable. Breakfast was less than average.
Reviewed on Mar 22, 2026
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)
1801 Atlantic Ave Virginia Beach VA
Fully refundable
$108 nightly
The price is $127 total per night from Mar 25 to Mar 26
$127 total
Mar 25 - Mar 26
Total with taxes and fees
8.4/10 Very Good! (2,507 reviews)
Ok room
Reviewed on Mar 21, 2026
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel
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! (1,221 reviews)
Clean, friendly front desk staff, next to boardwalk, surrounded by a variety of restaurants, shopping and entertainment. Easy parking, bottled water provided, easy walk to and from shopping areas. Very central. Ocean front room was convenient. Calypso bar and grill on site. I’d go back. I got a good ...
Reviewed on Mar 22, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.