Chesapeake City County Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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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.
The Lodge at Kiln Creek Resort

The Lodge at Kiln Creek Resort

3.5 out of 5
Central Newport News
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Norfolk (ORF)
9/10 Wonderful! (171 reviews)
Clean, quiet and convenient.

Reviewed on Jul. 8, 2025

Hampton Inn & Suites Newport News (Oyster Point)

Hampton Inn & Suites Newport News (Oyster Point)

2.5 out of 5
Central Newport News
per person
Oct 17 - Oct 26
found 2 hours ago
Roundtrip non-stop flight included
Québec (YQB) to Norfolk (ORF)
8.8/10 Excellent! (543 reviews)
Great staff. The hotel is conveniently surrounded by restaurants and retail stores.

Reviewed on Jul. 3, 2025

Days Inn by Wyndham Hampton Near Coliseum Convention Center

Days Inn by Wyndham Hampton Near Coliseum Convention Center

2 out of 5
Coliseum Central
per person
Oct 17 - Oct 26
found 2 hours ago
Roundtrip non-stop flight included
Québec (YQB) to Norfolk (ORF)
5.8/10 (1,006 reviews)
Close to several beaches and activities. Decently priced

Reviewed on Jul. 17, 2025

Mulberry Inn

Mulberry Inn

2.5 out of 5
North Newport News
per person
Oct 17 - Oct 26
found 2 hours ago
Roundtrip non-stop flight included
Québec (YQB) to Norfolk (ORF)
7.6/10 Good! (672 reviews)
Very clean and comfortable

Reviewed on Jul. 30, 2025

Sunrise Inn By OYO Newport News US-60

Sunrise Inn By OYO Newport News US-60

2.5 out of 5
North Newport News
per person
Oct 17 - Oct 26
found 2 hours ago
Roundtrip non-stop flight included
Québec (YQB) to Norfolk (ORF)
4.6/10 (194 reviews)
We stayed for one night to be close to the fields for a softball tournament. It was fine for what we needed it for

Reviewed on Jun. 5, 2022

Chesapeake City County Hotel Deals

Holiday Inn & Suites Virginia Beach North Beach by IHG

Holiday Inn & Suites Virginia Beach North Beach by IHG

3 out of 5
3900 Atlantic Avenue, Virginia Beach, VA
Fully refundable
The price is CA $260 per night from Sep 1 to Sep 2
CA $260
CA $302 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (1,011 reviews)
"Great place to stay next to board walk and walking distance to stores!"

Reviewed on Jul. 30, 2025

Holiday Inn & Suites Virginia Beach North Beach by IHG
Surfbreak Virginia Beach Oceanfront, Ascend Hotel Collection

Surfbreak Virginia Beach Oceanfront, Ascend Hotel Collection

3 out of 5
1101 Atlantic Ave, Virginia Beach, VA
Fully refundableReserve now, pay when you stay
The price is CA $176 per night from Sep 1 to Sep 2
CA $176
CA $205 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (1,041 reviews)
"Very nice to see"

Reviewed on Jul. 30, 2025

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

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

3 out of 5
1801 Atlantic Ave, Virginia Beach, VA
Fully refundableReserve now, pay when you stay
The price is CA $201 per night from Sep 1 to Sep 2
CA $201
CA $234 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (2,220 reviews)
"Good"

Reviewed on Jul. 29, 2025

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA
See all 3,426 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Chesapeake City County vacation package cost?
Perhaps less than you might think — from just CA $1,011, 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.