Name: Wyndham Virginia Beach Oceanfront
Price range: $183 total
Rating: 7.8

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.

Sea Ranch Resort

Save 100% on your flight

$614

per person

Aug 10 - Aug 14

found 21 hours ago

Roundtrip flight included

Boston (BOS) to Norfolk (ORF)

8.6/10 Excellent! (1,003 reviews)

Very easy to check in room was ready when we got there. Rooms were clean. Staff was polite easy access to the beach and we also like that. We were only there for three days and we got a short term rental for that instead of having to book the whole week, we just wanted a long weekend we would recommend the sea ranch resort to anyone. We had a great time.

Reviewed on Jul 6, 2026

John Yancey Oceanfront Inn

$679

per person

Sep 24 - Sep 29

found 24 hours ago

Roundtrip flight included

New York (NYC) to Norfolk (ORF)

9.2/10 Wonderful! (1,912 reviews)

The property was older but very nice and very clean. The staff went above and beyond. This is our new place to stay at the Outer Banks!!

Reviewed on Jul 8, 2026

The Inn at Four Eleven York

West Freemason

Save 100% on your flight

$1,008

per person

Sep 23 - Sep 28

found 1 hour ago

Roundtrip flight included

Dallas (DFW) to Norfolk (ORF)

10/10 Exceptional! (109 reviews)

The staff was extremely helpful and the room was incredibly lovely. Would definitely recommend and stay back in this hotel anytime.

Reviewed on Jun 6, 2026

Ambassadors Inn & Suites

Northeast Virginia Beach

Save 100% on your flight

$1,508

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Norfolk (ORF)

6/10 (1,005 reviews)

Management team is horrible! Would not recommend to a roach.

Reviewed on Jul 7, 2026

Holiday Inn & Suites Virginia Beach North Beach by IHG

Northeast Virginia Beach

$655

per person

Sep 20 - Sep 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Norfolk (ORF)

8/10 Very Good! (1,403 reviews)

Housekeeping never vacuumed despite “housekeeping every day”. Property is starting to show its age. The indoor pool did not look completely clean. Won’t be back there

Reviewed on Jul 8, 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

Hyatt Studios Chesapeake

101 Volvo Parkway Chesapeake VA

$140 nightly

$163 total

Jul 26 - Jul 27

Total with taxes and fees

7.8/10 Good! (24 reviews)

"Check in July 2nd and Departed July 6th newer hotel everything was still fairly new spotless up to date dishwasher refrigerator stove top electric and microwave oven good size flat screen television and comfortable bed and couch nice clean also bed couch at that walk in shower space decent I am glad ..."

Reviewed on Jul 8, 2026

Wingate by Wyndham Chesapeake

817 Greenbrier Circle Chesapeake VA

Fully refundableReserve now, pay when you stay

$122 nightly

$142 total

Aug 2 - Aug 3

Total with taxes and fees

7.8/10 Good! (1,110 reviews)

"The room was very nice, roomy and comfortable."

Reviewed on Jul 7, 2026

Wyndham Virginia Beach Oceanfront

5700 Atlantic Ave Virginia Beach VA

$158 nightly

$183 total

Jul 22 - Jul 23

Total with taxes and fees

7.8/10 Good! (1,878 reviews)

"Terrible staff"

Reviewed on Jul 8, 2026

See all 3,436 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

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.

See properties