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.
Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Northeast Virginia Beach
Price was CA $1,593, price is now CA $1,246 per person
CA $1,246
per person
May 26 - May 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Norfolk (ORF)
8.6/10 Excellent! (1,003 reviews)
This was a convenient location right on the boardwalk. The rooms were in good repair and looked clean. The front desk instructs you to talk to the concierge desk for some "welcome coupons," but it was a chance for them to invite you to a timeshare presentation. I walked over and ended up skipping talking to them after I heard the conversation with the couple in front of me. The kids enjoyed the pool and looking out at the ocean. The balcony has 2 chairs and a small table, but you could probably squeeze in 1 or 2 more chairs if you brought your own. It was a bit noisy from the restaurant downstairs, which has a patio with music playing but we brought a sound machine for the kids.

Reviewed on Apr 5, 2026

Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Price was CA $2,050, price is now CA $1,427 per person
CA $1,427
per person
Jun 29 - Jul 4
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Norfolk (ORF)
8.6/10 Excellent! (1,000 reviews)
The room was nice and the bed was comfortable. Beautiful ocean view and we had a good view of dolphins swimming up the coast on Monday morning. The only reason I didn't give 5 stars was that the check-out person at the front desk barely made eye contact and never asked how our stay was.

Reviewed on Apr 5, 2026

John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Price was CA $2,196, price is now CA $1,566 per person
CA $1,566
per person
Jun 29 - Jul 4
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Norfolk (ORF)
9/10 Wonderful! (1,868 reviews)
Great location and super clean room. We can’t wait to book our next stay!

Reviewed on Apr 4, 2026

Pamlico Station Edgecamp

Pamlico Station Edgecamp

2 out of 5
South Rodanthe
Price was CA $2,520, price is now CA $1,857 per person
CA $1,857
per person
Jun 29 - Jul 4
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Norfolk (ORF)
9.4/10 Exceptional! (24 reviews)
We came out for our anniversary and had a wonderful time! The sauna and cold plunges were being repaired, which was disappointing, but understandable to service them in the off season. It was quiet and very relaxing and our text to the concierge was very quick!

Reviewed on Mar 30, 2026

The Colony at Virginia Beach

The Colony at Virginia Beach

3 out of 5
Northeast Virginia Beach
Price was CA $1,887, price is now CA $1,483 per person
CA $1,483
per person
May 26 - May 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Norfolk (ORF)
8.8/10 Excellent! (13 reviews)
Clean room; wonderful hospitality staff

Reviewed on Mar 13, 2026

Chesapeake City County Hotel Deals

Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake

2.5 out of 5
817 Greenbrier Circle Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is CA $127 per night from Apr 19 to Apr 20
CA $127
CA $149 total
Apr 19 - Apr 20
includes taxes & fees
8/10 Very Good! (1,005 reviews)
Yes

Reviewed on Apr 6, 2026

Wingate by Wyndham Chesapeake
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

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

3 out of 5
1801 Atlantic Ave Virginia Beach VA
Fully refundable
The price is CA $173 per night from Apr 20 to Apr 21
CA $173
CA $202 total
Apr 20 - Apr 21
includes taxes & fees
8.4/10 Very Good! (2,535 reviews)
Clean room, beautiful view from room , sufficient breakfast , courteous staffs . We had excellent experience during the stay , we will visit again .

Reviewed on Apr 6, 2026

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)
Hyatt Place Virginia Beach / Oceanfront

Hyatt Place Virginia Beach / Oceanfront

3 out of 5
3601 ATLANTIC AVENUE Virginia Beach VA
Fully refundableReserve now, pay when you stay
The price is CA $177 per night from Apr 19 to Apr 20
CA $177
CA $206 total
Apr 19 - Apr 20
includes taxes & fees
9.4/10 Exceptional! (2,214 reviews)
Wonderful experience

Reviewed on Apr 5, 2026

Hyatt Place Virginia Beach / Oceanfront
See all 3,468 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 $1,246, 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.