Chesapeake City County Vacation Packages 2026 from $605

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

Chesapeake

Vacations

Chesapeake City County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

The Ocean Key Virginia Beach Resort

Northeast Virginia Beach

$605

per person

Mar 24 - Mar 29

found 4 hours ago

Roundtrip flight included

Detroit (DTW) 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 business center, laundry facilities, and free newspapers are also on offer.

Boardwalk Resort and Villas

Northeast Virginia Beach

Save 100% on your flight

$775

per person

Mar 28 - Apr 2

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.

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Northeast Virginia Beach

$626

per person

Mar 24 - Mar 29

found 4 hours ago

Roundtrip flight included

Detroit (DTW) to Norfolk (ORF)

This aparthotel 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.

Hilton Norfolk The Main

Downtown Norfolk

$748

per person

Mar 3 - Mar 7

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Norfolk (ORF)

This hotel features 3 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, express check-out, and valet parking. You'll appreciate the a rooftop terrace, bar/lounge, and convenience store.

The Atrium Resort, Virginia Beach by Vacatia

Northeast Virginia Beach

$644

per person

Mar 28 - Apr 2

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Norfolk (ORF)

This aparthotel features an indoor pool and a 24-hour gym. Guests will appreciate free perks like free self parking and WiFi in public areas. Express check-in, express check-out, and laundry facilities are also on offer.

Top Chesapeake City County hotels deals

Wingate by Wyndham Chesapeake

817 Greenbrier Circle Chesapeake VA

Free Cancellation

Reserve now, pay when you stay

$75 nightly

$88 total

Jan 18 - Jan 19

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

721 Conference Center Drive Chesapeake VA

Free Cancellation

$83 nightly

$97 total

Jan 25 - Jan 26

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

Fairfield Inn and Suites By Marriott Chesapeake

1560 Crossways Blvd Chesapeake VA

Free Cancellation

Reserve now, pay when you stay

$80 nightly

$94 total

Jan 25 - Jan 26

Total with taxes and fees

This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

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

1801 Atlantic Ave Virginia Beach VA

Free Cancellation

$91 nightly

$107 total

Jan 15 - Jan 16

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

3601 ATLANTIC AVENUE Virginia Beach VA

Free Cancellation

Reserve now, pay when you stay

$100 nightly

$117 total

Jan 29 - Jan 30

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

SureStay Hotel by Best Western Virginia Beach Royal Clipper

3508 Atlantic Ave Virginia Beach VA

Free Cancellation

Reserve now, pay when you stay

$63 nightly

$74 total

Jan 20 - Jan 21

Total with taxes and fees

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Staff at the 24-hour front desk can provide around-the-clock assistance.

Pool

Breakfast included

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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.

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Frequently asked questions

How much are vacation packages to Chesapeake City County?

Starting from as low as $605, 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.