Deals on vacations and trips to Chesapeake City County

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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 $676, price is now $504 per person
$504
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Chicago (CHI) 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.
John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Price was $764, price is now $513 per person
$513
per person
Nov 17 - Nov 24
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.
Blackbeard's Lodge

Blackbeard's Lodge

3.5 out of 5
Price was $1,091, price is now $843 per person
$843
per person
Nov 17 - Nov 24
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Norfolk (ORF)
A seasonal outdoor pool, free self parking, and barbecue grills are featured at this hotel. Guests will appreciate perks like free WiFi and a free airport shuttle. A picnic area and luggage storage are also provided.
The Burrus House Inn Waterfront Suites

The Burrus House Inn Waterfront Suites

3 out of 5
Save 100% on your flight
Price was $1,924, price is now $1,494 per person
$1,494
per person
Nov 17 - Nov 24
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Norfolk (ORF)
This bed & breakfast features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free on-the-go breakfast each morning. A snack bar/deli, express check-in, and express check-out are also on offer.
Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Price was $756, price is now $595 per person
$595
per person
Nov 17 - Nov 24
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.

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 8 - Sep 9
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
Free Cancellation
Reserve now, pay when you stay
$80 nightly
The price is $94 total per night
$94 total
Oct 1 - Oct 2
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
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
$127 nightly
The price is $148 total per night
$148 total
Oct 1 - Oct 2
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 27 - Sep 28
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
Holiday Inn Va Beach-Oceanside (21st St) by IHG

Holiday Inn Va Beach-Oceanside (21st St) by IHG

3 out of 5
2101 Atlantic Avenue Virginia Beach VA
Free Cancellation
$119 nightly
The price is $139 total per night
$139 total
Sep 30 - Oct 1
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.
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
$91 nightly
The price is $107 total per night
$107 total
Sep 30 - Oct 1
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
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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 $504, 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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