Deals on vacations and trips to Chesapeake City County

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Chesapeake Square Mall

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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 $846, price is now $623 per person
$623
per person
Mar 28 - Apr 3
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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.
Sanderling Resort Residences

Sanderling Resort Residences

4 out of 5
Save 100% on your flight
Price was $2,506, price is now $1,688 per person
$1,688
per person
Mar 14 - Mar 17
found 3 hours ago
Roundtrip flight included
Minneapolis (MSP) to Norfolk (ORF)
A full-service spa, 2 restaurants, and 2 outdoor pools are all featured at this smoke-free resort. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. Family-friendly amenities include a children's pool and kid-friendly dining, along with kayaking.
Ocean 27

Ocean 27

2.5 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $2,603, price is now $1,903 per person
$1,903
per person
Mar 17 - Mar 21
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Norfolk (ORF)
A seasonal outdoor pool is featured at this hotel, along with free self parking. WiFi in public areas is free. A terrace and luggage storage are also provided.
The Sanderling

The Sanderling

4 out of 5
Price was $1,092, price is now $847 per person
$847
per person
Apr 8 - Apr 12
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Norfolk (ORF)
A full-service spa, 2 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. Enjoy the 2 hot tubs and perks like free WiFi.
Pamlico Station Edgecamp

Pamlico Station Edgecamp

2 out of 5
South Rodanthe
Price was $903, price is now $704 per person
$704
per person
Mar 14 - Mar 17
found 3 hours ago
Roundtrip flight included
Minneapolis (MSP) to Norfolk (ORF)
This hotel features a hot tub and a sauna. Free self parking and concierge services are also offered on site.

Top Chesapeake City County hotels deals

Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake

2.5 out of 5
817 Greenbrier Circle Chesapeake VA
Free Cancellation
Reserve now, pay when you stay
$75 nightly
The price is $88 total per night
$88 total
Feb 1 - Feb 2
Total with taxes and fees
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 hot tub and free perks like continental breakfast and free self parking.
Pool
Hot Tub
Holiday Inn Express Chesapeake - Norfolk by IHG

Holiday Inn Express Chesapeake - Norfolk by IHG

2.5 out of 5
721 Conference Center Drive Chesapeake VA
Free Cancellation
$83 nightly
The price is $97 total per night
$97 total
Feb 1 - Feb 2
Total with taxes and fees
This hotel features a gym and a seasonal outdoor pool. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A 24-hour business center, luggage storage, and laundry facilities are also on offer.
Pool
Breakfast included
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

3 out of 5
1801 Atlantic Ave Virginia Beach VA
Free Cancellation
$90 nightly
The price is $106 total per night
$106 total
Jan 27 - Jan 28
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free on-the-go breakfast each morning.
Pool
Breakfast included
Hyatt Place Virginia Beach / Oceanfront

Hyatt Place Virginia Beach / Oceanfront

3 out of 5
3601 ATLANTIC AVENUE Virginia Beach VA
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $129 total per night
$129 total
Feb 1 - Feb 2
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 free buffet breakfast each morning.
Pool
Breakfast 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
$130 nightly
The price is $152 total per night
$152 total
Feb 24 - Feb 25
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 gym and conveniences like a 24-hour front desk 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
$92 nightly
The price is $107 total per night
$107 total
Feb 1 - Feb 2
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
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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.

Photos of local treasures

Browse Chesapeake City County vacation photos for more inspiration

Greenbrier Mall
Greenbrier Mall
Greenbrier Mall
Greenbrier Mall
Greenbrier Mall

Frequently asked questions

How much are vacation packages to Chesapeake City County?
Starting from as low as $623, 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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