Deals on vacations and trips to Chesapeake City County

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

Chesapeake

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Chesapeake

Chesapeake City County flight + hotel vacation packages

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 $328, price is now $258 per person
$258
per person
Jan 15 - Jan 18
found 8 hours ago
Roundtrip flight included
Orlando (ORL) to Norfolk (ORF)
This hotel features an indoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. A business center, express check-out, and laundry facilities are also on offer.
Holiday Inn Express Hotel & Suites Norfolk Airport by IHG

Holiday Inn Express Hotel & Suites Norfolk Airport by IHG

2.5 out of 5
Price was $494, price is now $399 per person
$399
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Norfolk (ORF)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.
The Barclay Towers Resort Hotel

The Barclay Towers Resort Hotel

2.5 out of 5
Northeast Virginia Beach
Price was $372, price is now $305 per person
$305
per person
Jan 15 - Jan 18
found 8 hours ago
Roundtrip flight included
Orlando (ORL) 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.
Residence Inn by Marriott Norfolk Airport

Residence Inn by Marriott Norfolk Airport

3 out of 5
Price was $434, price is now $358 per person
$358
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Norfolk (ORF)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free buffet breakfast is served.
The Inn at Four Eleven York

The Inn at Four Eleven York

4 out of 5
West Freemason
Price was $761, price is now $628 per person
$628
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Norfolk (ORF)
A restaurant and a bar/lounge are featured at this bed & breakfast. There's no skimping on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. A terrace, a garden, and a snack bar/deli are also on offer.

Top Chesapeake City County hotels deals

Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk

2.5 out of 5
1550 Crossways Blvd Chesapeake VA
Free Cancellation
$89 nightly
The price is $104 total per night
$104 total
Nov 29 - Nov 30
Total with taxes and fees
This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
YourSpace Hotels Chesapeake

YourSpace Hotels Chesapeake

3 out of 5
2137 Starmount Parkway Chesapeake VA
Free Cancellation
Reserve now, pay when you stay
$87 nightly
The price is $102 total per night
$102 total
Nov 8 - Nov 9
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the express check-in. A 24-hour gym and locker space are also provided.
Pet friendly
Parking included
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
Get rates
This hotel features a restaurant, a seasonal outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Free self parking, a library, and dry cleaning are also offered.
Pool
Parking included
Hilton Vacation Club Oceanaire Virginia Beach

Hilton Vacation Club Oceanaire Virginia Beach

3.5 out of 5
3421 Atlantic Ave Virginia Beach VA
Free Cancellation
Reserve now, pay when you stay
$100 nightly
The price is $117 total per night
$117 total
Nov 29 - Nov 30
Total with taxes and fees
This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. You'll appreciate the gym, poolside bar, and laundry facilities.
Pool
Free WiFi
Hilton Vacation Club Ocean Beach Club Virginia Beach

Hilton Vacation Club Ocean Beach Club Virginia Beach

3.5 out of 5
3401 Atlantic Ave Virginia Beach VA
Free Cancellation
Reserve now, pay when you stay
$88 nightly
The price is $103 total per night
$103 total
Nov 5 - Nov 6
Total with taxes and fees
This smoke-free hotel features 2 indoor pools, an outdoor pool, and a restaurant. Enjoy the 24-hour gym and perks like free WiFi. There's a beach bar on site, and laundry facilities and concierge services are also provided.
Pool
Free WiFi
Budget Inn Norfolk Va

Budget Inn Norfolk Va

2 out of 5
9601 4th View Street Norfolk VA
Free Cancellation
Reserve now, pay when you stay
$55 nightly
The price is $66 total per night
$66 total
Nov 5 - Nov 6
Total with taxes and fees
This motel features a snack bar/deli, laundry facilities, and free self parking. WiFi in public areas is provided and the front desk is staffed around-the-clock.
Parking included
Air conditioning
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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 large building with a prominent arched entrance and a green roof.

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.
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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 $258, 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.

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