Chesapeake City County Vacation Packages

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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 Chesapeake City County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Sea Ranch Resort
Outer Banks Beach Club
John Yancey Oceanfront Inn
Delta Hotels by Marriott Virginia Beach Waterfront Suites
The Atrium Resort, Virginia Beach by Vacatia

Chesapeake City County Hotel Deals

Hyatt Studios Chesapeake

Hyatt Studios Chesapeake

2 out of 5
101 Volvo Parkway Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is CA $248 per night from Jul 22 to Jul 23
CA $248
per night
Jul 22 - Jul 23
7.8/10 Good! (25 reviews)
"Literally one of the best experiences."

Reviewed on Jul 9, 2026

Hyatt Studios Chesapeake
Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

3 out of 5
5700 Atlantic Ave Virginia Beach VA
Fully refundableReserve now, pay when you stay
The price is CA $214 per night from Jul 23 to Jul 24
CA $214
per night
Jul 23 - Jul 24
7.8/10 Good! (1,888 reviews)
"All in all, my stay was a good one with zero complaints. The staff was so nice, both at the front desk, and in the restaurant. Very attentive and accommodating! The location was perfect! Quiet, uncrowded, and easy to get to. It's in North VB so way more residential. I had an ocean view and it was ..."

Reviewed on Jul 9, 2026

Wyndham Virginia Beach Oceanfront
Crowne Plaza Virginia Beach Town Center by IHG

Crowne Plaza Virginia Beach Town Center by IHG

3.5 out of 5
4453 Bonney Rd Virginia Beach VA
Fully refundableReserve now, pay when you stay
The price is CA $144 per night from Aug 2 to Aug 3
CA $144
per night
Aug 2 - Aug 3
8.4/10 Very good! (400 reviews)
"The room was clean. The beds were very comfortable. The staff was friendly. Breakfast was good. Parking was sufficient."

Reviewed on Jul 9, 2026

Crowne Plaza Virginia Beach Town Center by IHG
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 CA $1,278, 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.

Stay near popular Chesapeake City County attractions

What to do in Chesapeake City County

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.