Chesapeake City County Vacations & Trips from ￥180,088

Book a Hotel + Flight or Car together to unlock savings

Photo by Kaylee Spinhirn

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ￥45,448 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

The Latest Chesapeake City County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Price was ￥194,760, price is now ￥180,088 per person
￥180,088
per person
Dec 26 - Dec 31
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Norfolk (ORF)
9/10 Wonderful! (1,744 reviews)
I had a very good and pleasant experience. Everything went smoothly, and the staff were friendly and professional.

Reviewed on Oct 6, 2025

Chesapeake City County Hotel Deals

Schooner Inn

Schooner Inn

2 out of 5
215 Atlantic Ave, Virginia Beach, VA
8.6/10 Excellent! (3,540 reviews)
"Awesome stay"

Reviewed on Oct 4, 2025

Get rates
Schooner Inn
Oceans 2700

Oceans 2700

2.5 out of 5
2700 Pacific Avenue, Virginia Beach, VA
Fully refundableReserve now, pay when you stay
7.8/10 Good! (1,477 reviews)
"Good location, some updates would be nice but overall good for the price"

Reviewed on Oct 3, 2025

Get rates
Oceans 2700
Delta Hotels by Marriott Virginia Beach Waterfront Suites

Delta Hotels by Marriott Virginia Beach Waterfront Suites

4 out of 5
2800 Shore Drive, Virginia Beach, VA
Fully refundableReserve now, pay when you stay
The price is ￥13,125 per night from Oct 26 to Oct 27
￥13,125
￥15,388 total
Oct 26 - Oct 27
includes taxes & fees
8.4/10 Very Good! (1,401 reviews)
"The staff was very friendly, beach access was wonderful. The whole peninsula lost power, which of course I don't blame anyone for, but I thought they would have had a generator hooked up for everything instead of just emergency lights in the hallways ONLY. The restaurant in the hotel was extremely ..."

Reviewed on Oct 4, 2025

Delta Hotels by Marriott Virginia Beach Waterfront Suites
See all 3,430 properties in Chesapeake City County
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.

Frequently asked questions

How much does a Chesapeake City County vacation package cost?
Perhaps less than you might think — from just ￥180,088, actually! By bundling hotels, flights and car rentals into a custom-built package, your getaway to Chesapeake City County is just clicks away.
How do I get a cheap travel package to Chesapeake City County?
Find flights that suit your schedule, add a hotel to your booking and watch the savings rack up with a Chesapeake City County vacation package. It's as easy as that! From flights and hotels to activities and rental cars, Expedia makes traveling on a budget easy. And with over 550 partner airlines and 1,000,000 properties globally to choose from, you'll never be short of choice.
What are the top hotels in Chesapeake City County?
Hyatt Place Chesapeake and Aloft Chesapeake are a couple of welcoming options in Chesapeake. A key stop on any good Chesapeake City County itinerary, we recommend taking the time to really explore this impressive city.
How far in advance should I book my Chesapeake City County vacation?
Search Expedia to compare international airfares as soon as you've got your travel dates. You can normally purchase a seat up to 12 months before departure. If you can't see your preferred air carrier, or you've left things to the last moment, fear not. Cheap tickets to Chesapeake City County occasionally appear within weeks of departure.
What does an Expedia Chesapeake City County travel package include?
You can choose from any combination of rental cars, hotels and flights. Once you've made your booking, you can add activities and experiences. Want to pick your fare class? That's also possible. The choice is all yours when it comes to putting together your dream Chesapeake City County getaway.
What should I know before booking a Chesapeake City County travel package?
Booking all the parts of your escape together is a smart way to save. Combine your car rentals, flights and hotels into a handy little package. But you're not limited to hotels. Expedia offers all sorts of properties, including vacation rentals such as beach villas and city residences. The list is almost endless!
Can I choose my airline with a Chesapeake City County Expedia vacation package?
Expedia offers access to more than 550 airline partners globally, so you sure can! Just select your preferred carrier and craft your ideal Chesapeake City County trip.
If I'm not able to travel, can I cancel my Chesapeake City County vacation package?
If your vacation plans in Chesapeake City County have changed, it's a relief to know that it is possible to cancel your booking. If you booked in the last 24 hours, you may be eligible to receive a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may impose a cancellation fee. For more details, check our Customer Service Portal.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.