
Chesapeake City County Vacations & Trips from $614
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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
Save 100% on your flight
Price was $892, price is now $614 per person
$614
per person
Aug 10 - Aug 14
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.6/10 Excellent! (1,003 reviews)
Very easy to check in room was ready when we got there. Rooms were clean. Staff was polite easy access to the beach and we also like that. We were only there for three days and we got a short term rental for that instead of having to book the whole week, we just wanted a long weekend we would recommend the sea ranch resort to anyone. We had a great time.
Reviewed on Jul 6, 2026

John Yancey Oceanfront Inn
Price was $900, price is now $679 per person
$679
per person
Sep 24 - Sep 29
found 24 hours ago
Roundtrip flight included
New York (NYC) to Norfolk (ORF)
9.2/10 Wonderful! (1,912 reviews)
The property was older but very nice and very clean. The staff went above and beyond. This is our new place to stay at the Outer Banks!!
Reviewed on Jul 8, 2026

The Inn at Four Eleven York
West Freemason
Save 100% on your flight
Price was $1,329, price is now $1,008 per person
$1,008
per person
Sep 23 - Sep 28
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to Norfolk (ORF)
10/10 Exceptional! (109 reviews)
The staff was extremely helpful and the room was incredibly lovely. Would definitely recommend and stay back in this hotel anytime.
Reviewed on Jun 6, 2026

Ambassadors Inn & Suites
Northeast Virginia Beach
Save 100% on your flight
Price was $1,983, price is now $1,508 per person
$1,508
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Norfolk (ORF)
6/10 (1,005 reviews)
Management team is horrible! Would not recommend to a roach.
Reviewed on Jul 7, 2026

Holiday Inn & Suites Virginia Beach North Beach by IHG
Northeast Virginia Beach
Price was $851, price is now $655 per person
$655
per person
Sep 20 - Sep 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8/10 Very Good! (1,403 reviews)
Housekeeping never vacuumed despite “housekeeping every day”. Property is starting to show its age.
The indoor pool did not look completely clean.
Won’t be back there
Reviewed on Jul 8, 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

Hyatt Studios Chesapeake
101 Volvo Parkway Chesapeake VA
$140 nightly
The price is $163 total per night from Jul 26 to Jul 27
$163 total
Jul 26 - Jul 27
Total with taxes and fees
7.8/10 Good! (24 reviews)
"Check in July 2nd and Departed July 6th newer hotel everything was still fairly new spotless up to date dishwasher refrigerator stove top electric and microwave oven good size flat screen television and comfortable bed and couch nice clean also bed couch at that walk in shower space decent I am glad ..."
Reviewed on Jul 8, 2026

Wingate by Wyndham Chesapeake
817 Greenbrier Circle Chesapeake VA
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $142 total per night from Aug 2 to Aug 3
$142 total
Aug 2 - Aug 3
Total with taxes and fees
7.8/10 Good! (1,110 reviews)
"The room was very nice, roomy and comfortable."
Reviewed on Jul 7, 2026

Wyndham Virginia Beach Oceanfront
5700 Atlantic Ave Virginia Beach VA
$158 nightly
The price is $183 total per night from Jul 22 to Jul 23
$183 total
Jul 22 - Jul 23
Total with taxes and fees
7.8/10 Good! (1,878 reviews)
"Terrible staff"
Reviewed on Jul 8, 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
What to do in Chesapeake City County

City Cruises Norfolk: Signature Dinner Cruise
$84
per adult
76% of travellers recommend

Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin
$43
per adult
100% of travellers recommend

City Cruises Norfolk: Signature Brunch Cruise
$83
per adult
88% of travellers recommend
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