Deals on vacations and trips to Chesapeake City County

Save when you book Chesapeake City County, VA package deals

Choose two or more items and save on your trip:

Search vacation packages deals in Chesapeake City County's top destinations

A golf course, a large building complex, and a marina by a river.

Chesapeake

Vacations
Chesapeake

Chesapeake City County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Ocean Key Virginia Beach Resort

The Ocean Key Virginia Beach Resort

3 out of 5
Northeast Virginia Beach
Price was $623, price is now $488 per person
$488
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Norfolk (ORF)
This aparthotel features an indoor pool, a gym, and a restaurant. Guests will appreciate free perks like free self parking and WiFi in public areas. A safe deposit box is provided and the front desk is staffed around-the-clock.
The Barclay Towers Resort Hotel

The Barclay Towers Resort Hotel

2.5 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $856, price is now $613 per person
$613
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Norfolk (ORF)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and perks like free self parking and free WiFi. Enjoy the hot tub and conveniences like a 24-hour front desk and laundry facilities.
The Capes Hotel

The Capes Hotel

3 out of 5
Northeast Virginia Beach
Price was $771, price is now $592 per person
$592
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Norfolk (ORF)
A restaurant and an indoor pool are featured at this hotel. WiFi in public areas is free. A safe deposit box is provided and the front desk is staffed around-the-clock.
Ocean 27

Ocean 27

2.5 out of 5
Northeast Virginia Beach
Price was $816, price is now $637 per person
$637
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Norfolk (ORF)
A seasonal outdoor pool is featured at this hotel, along with self parking. WiFi in public areas is free. Express check-out is provided and the front desk is staffed around-the-clock.
LABH INC

LABH INC

2.5 out of 5
Price was $675, price is now $547 per person
$547
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Norfolk (ORF)
This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free continental breakfast each morning. Staff at the 24-hour front desk can provide around-the-clock assistance.

Top Chesapeake City County hotels deals

Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

3 out of 5
5700 Atlantic Ave Virginia Beach VA
Free Cancellation
Reserve now, pay when you stay
$86 nightly
The price is $100 total per night
$100 total
Aug 31 - Sep 1
Total with taxes and fees
This hotel features an indoor pool, a gym, and a restaurant. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. A bar/lounge, a 24-hour front desk, and a terrace are also provided.
Ocean Resort

Ocean Resort

2.5 out of 5
Atlantic Avenue,2417 Virginia Beach VA
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $115 total per night
$115 total
Sep 13 - Sep 14
Total with taxes and fees
An indoor pool is featured at this hotel, along with free self parking. WiFi in public areas is free. A terrace and a safe deposit box are also provided.
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
Free Cancellation
$93 nightly
The price is $109 total per night
$109 total
Sep 7 - Sep 8
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.
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
Free Cancellation
$159 nightly
The price is $185 total per night
$185 total
Sep 13 - Sep 14
Total with taxes and fees
This smoke-free hotel features 3 restaurants, 3 outdoor pools, and an indoor pool. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. There's fun for all ages with a lazy river and a free kid's club, and families will appreciate the onsite laundry facilities.
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

3 out of 5
1101 Atlantic Ave Virginia Beach VA
Free Cancellation
$101 nightly
The price is $118 total per night
$118 total
Sep 9 - Sep 10
Total with taxes and fees
This hotel features a restaurant, a seasonal outdoor pool, and a bar/lounge. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Guests will appreciate free perks like free self parking and WiFi in public areas.
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
Free Cancellation
Reserve now, pay when you stay
$143 nightly
The price is $166 total per night
$166 total
Sep 13 - Sep 14
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and laundry facilities.
Don't see what you're looking for?
See all available properties in Chesapeake City County
View all properties
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.

Stay near popular Chesapeake City County attractions

A CVS store with a large archway and a red star logo.

Greenbrier Mall

8.4/10 (837 reviews)
You can browse for the perfect souvenirs at Greenbrier Mall during your visit to Chesapeake. Stroll along the beautiful beaches or attend a sporting event in the area.
See properties

Photos of local treasures

Browse Chesapeake City County vacation photos for more inspiration

A large building with a prominent arched entrance and a green roof.
A building with a large arched entrance, surrounded by trees and a parking lot.
A building with a large arched entrance, a sign reading "Dillard's," and well-maintained landscaping.
A modern building with a curved facade and a sign reading "Chesapeake Conference Center".
A modern building with a curved glass facade and a sign reading "Chesapeake Conference Center."

Frequently asked questions

How much are vacation packages to Chesapeake City County?
Starting from as low as $488, hotel and flight packages are the perfect way to stretch your travel budget. Chesapeake City County, here you come!
Where can I get the best vacation package deals for Chesapeake City County?
You'll come across an excellent range of Chesapeake City County package deals on Travelocity. With as many as 400 airlines and 1,000,000 properties worldwide, arranging the ultimate escape will be simple.
Why should I book my Chesapeake City County vacation bundle via Travelocity?
You'll not only enjoy big savings, but you'll also have access to our 24/7 customer support, top-notch service and a Price Match Guarantee. Explore every nook-and-cranny across the world, discover hidden treasures and create unforgettable memories — we'll take care of the important details.
Can I save money on my Chesapeake City County car rental if I combine it with a hotel or flight?
Certainly. And our Chesapeake City County vacation packages are the ideal way to do it. In just a few clicks you can save cash and time by booking everything in one place. Collect the keys to your rental car and feel the freedom of the open road. Need to fill your itinerary? Add a few tours to your package and make savings on those too.
Which airport is best for Chesapeake City County?
Traveling to Chesapeake City County will see you step off the plane at Norfolk Intl. Airport (ORF) or Newport News - Williamsburg Intl. Airport (PHF).
What is there to do in Chesapeake City County?
Chesapeake City County boasts hidden gems at every corner, however make sure you plan a trip to Chesapeake City Park and Chesapeake City Hall while you're in town. These two attractions shouldn't be missed.

Explore More Ways to Travel with Travelocity