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.
TRU by Hilton Chesapeake, VA

TRU by Hilton Chesapeake, VA

2.5 out of 5
Greenbrier
Price was CA $1,870, price is now CA $1,381 per person
CA $1,381
per person
Jun 25 - Jul 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
8.6/10 Excellent! (462 reviews)
Property was clean. Staff was nice. Centrally located. Lots of stores nearby. Plenty of places to eat nearby. Breakfast in the morning was good. Reasonably priced

Reviewed on May 17, 2026

Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Price was CA $2,460, price is now CA $1,722 per person
CA $1,722
per person
Aug 8 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Norfolk (ORF)
8.6/10 Excellent! (1,012 reviews)
Nice place, right on the beach

Reviewed on May 9, 2026

Pamlico Station Edgecamp

Pamlico Station Edgecamp

2 out of 5
South Rodanthe
Price was CA $3,474, price is now CA $2,470 per person
CA $2,470
per person
Aug 8 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Norfolk (ORF)
9.4/10 Exceptional! (33 reviews)
Very unique spot. Javi the concierge was super helpful. Staff was also on site periodically or could be called to come if needed. Unit was beautiful and clean with lots of amenities. We especially liked the hot tub and sauna on the deck

Reviewed on May 18, 2026

Sea Scape Beach and Golf Villas

Sea Scape Beach and Golf Villas

3.5 out of 5
Sea Scape
Price was CA $2,896, price is now CA $2,126 per person
CA $2,126
per person
Aug 8 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Norfolk (ORF)
9.2/10 Wonderful! (154 reviews)
They give towels for the pool

Reviewed on May 24, 2026

Sanderling Resort Residences

Sanderling Resort Residences

4 out of 5
Price was CA $11,219, price is now CA $8,421 per person
CA $8,421
per person
Aug 8 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Norfolk (ORF)
No reviews

Chesapeake City County Hotel Deals

Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake

3 out of 5
817 Greenbrier Circle Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is CA $170 per night from May 31 to Jun 1
CA $170
CA $198 total
May 31 - Jun 1
includes taxes & fees
8/10 Very Good! (1,051 reviews)
"The hotel was clean, but older and not updated. The Jacuzzi in the pool area was not functional, and the outlet in my bathroom was not functioning so no use of hairdryer or other electric small appliances. Of the three Wyndham properties I stayed in on my travels, this was the most expensive but ..."

Reviewed on May 24, 2026

Wingate by Wyndham 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 $134 per night from May 31 to Jun 1
CA $134
CA $167 total
May 31 - Jun 1
includes taxes & fees
7.8/10 Good! (1,830 reviews)
"Stayed in the Jr. Executive Suite and loved the additional space the room offered. There are few photos but the 2nd floor suite (there are only 2 but the 2nd floor is the one I stayed in) has 2 separate balconies, ocean view, party over patio area, view is basically dead center of hotel with panoramic ..."

Reviewed on May 24, 2026

Wyndham 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 $275 per night from May 31 to Jun 1
CA $275
CA $319 total
May 31 - Jun 1
includes taxes & fees
9.4/10 Exceptional! (2,282 reviews)
"It was perfect , clean and beautifull"

Reviewed on May 23, 2026

Hyatt Place Virginia Beach / Oceanfront
See all 3,463 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
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Frequently asked questions

How much does a Chesapeake City County vacation package cost?
Perhaps less than you might think — from just CA $1,381, 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.