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 $693, price is now $516 per person
$516
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Denver (DEN) 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.
Sea Scape Beach and Golf Villas

Sea Scape Beach and Golf Villas

3.5 out of 5
Sea Scape
Price was $1,092, price is now $765 per person
$765
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Norfolk (ORF)
2 outdoor pools, an indoor pool, and an outdoor tennis court are all featured at this smoke-free condo. Bring the family and enjoy the mini golf, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.
John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Price was $1,101, price is now $811 per person
$811
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Norfolk (ORF)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Families will appreciate the playground and barbecue grills. There's an outdoor pool on site, and a terrace and a picnic area are also provided.
Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Price was $829, price is now $622 per person
$622
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Norfolk (ORF)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference center. Enjoy the gym and perks like free self parking.
The Colony at Virginia Beach

The Colony at Virginia Beach

3 out of 5
Northeast Virginia Beach
Price was $871, price is now $679 per person
$679
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to Norfolk (ORF)
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this condo. WiFi in public areas is free. Barbecue grills are provided for your convenience.

Top Chesapeake City County hotels deals

Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

3 out of 5
5700 Atlantic Ave Virginia Beach VA
$102 nightly
The price is $119 total per night
$119 total
Sep 2 - Sep 3
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.
Pool
Pet friendly
Ocean Resort

Ocean Resort

2.5 out of 5
Atlantic Avenue,2417 Virginia Beach VA
$93 nightly
The price is $109 total per night
$109 total
Sep 20 - Sep 21
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.
Pool
Parking included
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
$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.
Pool
Free WiFi
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
$164 nightly
The price is $191 total per night
$191 total
Sep 24 - Sep 25
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.
Pool
Free WiFi
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
$84 nightly
The price is $99 total per night
$99 total
Sep 20 - Sep 21
Total with taxes and fees
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
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.
Pool
Pet friendly
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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 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.
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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 $516, 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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