Name: Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel
Rating: 8.4

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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.

Barrier Island Station

$502

per person

Dec 10 - Dec 15

found 21 hours ago

Roundtrip flight included

New York (NYC) to Norfolk (ORF)

7.8/10 Good! (319 reviews)

The Inn at Four Eleven York

West Freemason

$1,020

per person

Jan 10 - Jan 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

10/10 Exceptional! (116 reviews)

Blackbeard's Lodge

$685

per person

Dec 10 - Dec 15

found 21 hours ago

Roundtrip flight included

New York (NYC) to Norfolk (ORF)

8.4/10 Very Good! (426 reviews)

Location was great beds were comfy view was great

Reviewed on Nov 1, 2026

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Northeast Virginia Beach

$713

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

$598

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)

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

$98 total

Nov 29 - Nov 30

Total with taxes and fees

9/10 Wonderful! (1,158 reviews)

"Put us right next to the elevator, exit door, ice machine. We heard every movement in the hallway ALL NIGHT LONG. Breakfast staff was AMAZING! Absolutely the highlight of our stay."

Reviewed on Nov 9, 2026

YourSpace Hotels Chesapeake

2137 Starmount Parkway Chesapeake VA

Fully refundableReserve now, pay when you stay

$87 nightly

$102 total

Nov 14 - Nov 15

Total with taxes and fees

9.6/10 Exceptional! (283 reviews)

"Love this place! One of my favorite places to stay on the East Coast."

Reviewed on Nov 10, 2026

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

1101 Atlantic Ave Virginia Beach VA

8.4/10 Very Good! (1,629 reviews)

"Good hotel on boardwalk, friendly staff."

Reviewed on Nov 9, 2026

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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