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Your Chesapeake City County Vacation

Leave the planning to us with a Chesapeake City County vacation package. With everything organized before you leave home, the only thing left for you to do is relax and experience this destination's beauty and culture. Not sure where your first stop should be? Chesapeake is among the most popular cities to visit during a trip to Chesapeake City County. Expedia has hotels, flights and all your other travel needs to help you put together your very own customized Chesapeake City County vacation today.

Top destinations in Chesapeake City County

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

The Latest Chesapeake City County Vacation Packages

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

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Northeast Virginia Beach

$591

per person

Jan 19 - Jan 23

found 16 hours ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Norfolk (ORF)

8.2/10 Very Good! (1,447 reviews)

Holiday Inn & Suites Virginia Beach North Beach by IHG

Northeast Virginia Beach

$713

per person

Dec 20 - Dec 27

found 21 hours ago

Roundtrip flight included

Atlanta (ATL) to Norfolk (ORF)

8/10 Very Good! (1,584 reviews)

Hotel is under renovation- but has a million dollar view!

Reviewed on Oct 27, 2026

The Sitio

Northeast Virginia Beach

$708

per person

Dec 27 - Dec 30

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

9.4/10 Exceptional! (81 reviews)

Ocean View Inn

Cottage Line

$2,433

per person

Jan 19 - Jan 23

found 16 hours ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Norfolk (ORF)

6.2/10 (1,006 reviews)

Roaches and gross. Do not stay here beach is full of trash. Awful.

Reviewed on Oct 24, 2026

The Inn at Four Eleven York

West Freemason

$827

per person

Jan 19 - Jan 23

found 16 hours ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Norfolk (ORF)

10/10 Exceptional! (116 reviews)

We stayed for our honeymoon before embarking on our cruise to Bermuda out of Norfolk. The port was very close to the Inn. The Inn is beautiful and so romantic. The area around the Inn had several options for dining. The walkable area was so romantic with its old architecture and cobblestone streets. I would love to come and stay longer and experience their restaurants and the city of Norfolk. I would highly recommend the Inn to anyone wanting a place that is not a big box type hotel. If you want charm and romance this place is for you!!!!

Reviewed on Oct 20, 2026

Find the Best Chesapeake City County Vacation Packages

Chesapeake City County Essential Information

Language	English
Currency	U.S dollars
Closest Airport	Norfolk Intl. Airport (ORF)
Top Sights	Chesapeake City Park, Oak Grove Lake Park and Lake Drummond

Chesapeake City County Hotel Deals

Comfort Suites Chesapeake - Norfolk

1550 Crossways Blvd Chesapeake VA

Fully refundable

$84 nightly

$99 total

Nov 29 - Nov 30

Total with taxes and fees

YourSpace Hotels Chesapeake

2137 Starmount Parkway Chesapeake VA

Fully refundableReserve now, pay when you stay

$91 nightly

$107 total

Nov 8 - Nov 9

Total with taxes and fees

9.6/10 Exceptional! (268 reviews)

"Loved having a washer and dryer, super convenient. The staff was so friendly and the room was very comfortable. The sheets had some stains on them and the staff were prompt and apologetic on the issue."

Reviewed on Oct 29, 2026

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

1101 Atlantic Ave Virginia Beach VA

Get rates

See all 3,536 properties in Chesapeake City County

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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