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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 beach at sunset with a pier extending into the water.

The Latest Chesapeake City County Vacation Packages

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

Boardwalk Resort and Villas

Northeast Virginia Beach

$491

per person

Jan 10 - Jan 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

8.8/10 Excellent! (1,003 reviews)

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Northeast Virginia Beach

$655

per person

Jan 10 - Jan 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

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

Holiday Inn & Suites Virginia Beach North Beach by IHG

Northeast Virginia Beach

$540

per person

Jan 10 - Jan 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

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

The Colony at Virginia Beach

Northeast Virginia Beach

$630

per person

Jan 10 - Jan 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

9.2/10 Wonderful! (57 reviews)

Marriott Virginia Beach Oceanfront Resort

Northeast Virginia Beach

$864

per person

Jan 10 - Jan 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

9/10 Wonderful! (1,001 reviews)

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

Dec 8 - Dec 9

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 29 - Nov 30

Total with taxes and fees

9.6/10 Exceptional! (278 reviews)

"Great location and nice rooms."

Reviewed on Nov 8, 2026

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

1101 Atlantic Ave Virginia Beach VA

Get rates

See all 3,431 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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