The Best Luxury Hotels in Chesapeake, VA from ￥12,814 in 2026

Colorful sunset over riverside resort in Cambridge Maryland USA

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Our top choices for Chesapeake luxury hotels

The Historic Cavalier Hotel and Beach Club, Autograph Collection

Northeast Virginia Beach

￥98,091 total

includes taxes & fees

Jun 17 - Jun 18

The Founders Inn and Spa, Tapestry Collection by Hilton

Virginia Beach

Luxurious Virginia Beach retreat offers colonial charm, full-service spa, resort pools, and elegant gardens.

￥28,866 total

includes taxes & fees

Jun 15 - Jun 16

Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

Hilton Virginia Beach Oceanfront

Northeast Virginia Beach

￥56,020 total

includes taxes & fees

Jun 28 - Jun 29

Indoor pool, outdoor pool, open 7:00 AM to 11:00 PM, pool umbrellas

Marriott Virginia Beach Oceanfront Resort

Northeast Virginia Beach

￥62,780 total

includes taxes & fees

Jun 21 - Jun 22

3 restaurants; breakfast, lunch, dinner, and brunch served

Hilton Norfolk The Main

Downtown Norfolk

Riverside retreat offers rooftop terrace, 3 restaurants, and refined pool in Norfolk's cultural heart.

￥46,228 total

includes taxes & fees

Jun 23 - Jun 24

Doubletree by Hilton Hotel Norfolk Airport

Norfolk

Newly renovated luxury near Norfolk airport features plush beds, designer toiletries, and indoor pool.

￥27,364 total

includes taxes & fees

Jun 28 - Jun 29

The Westin Virginia Beach Town Center

Northwest

￥37,736 total

includes taxes & fees

Jun 14 - Jun 15

Delta Hotels by Marriott Virginia Beach Waterfront Suites

Northeast Virginia Beach

￥40,657 total

includes taxes & fees

Jun 15 - Jun 16

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Top Chesapeake Hotel Reviews

Wyndham Virginia Beach Oceanfront

6/10 Okay

"It would really have helped to have a buffet breakfast. The breakfast there for $18 was really bad bacon uncooked eggs looked old we left went elsewhere for breakfast. But at the price we paid per evening shortly bagels and coffee could’ve been provided for free."

Hilton Vacation Club Ocean Beach Club Virginia Beach

6/10 Okay

"We had a great stay but our freezer was broke and noisy, the hotel room floor was swept but hadn’t been mopped in a long long time our feet were immediately black and disgusting so we bought cheap slipper socks, and the kids pool was in need of some repairs and updating and warmer water! The other pool was adults only so I don’t know about that one but if you are going to limit where I can go with my kids atleast make the water WARM."

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

4/10 Poor

"The view was great right on the boardwalk. But they charged my card without me knowing it and they didn’t even know why. They were suppose to text me or let me know cause it happened on my last night they never did. It took four days to get my back account straightened back out. The pool was cold and full of sand where people came for the beach and jumped it. Never seen anyone cleaning it. Dirty bandaids were laying by the pool. Several of the brick around the pool were loss. They put a $250 deposit hold on your card and charge you $15 a day to park that isn’t included in your room. The door to the garage on your floor wasn’t working right. Instead of them fixing it they just left it unlocked."

Frequently asked questions

Are you searching for a great accommodation for your luxury holiday in Chesapeake?

Use Expedia to help you arrange a flight to Norfolk Intl. Airport (ORF) airport or Newport News - Williamsburg Intl. Airport (PHF) airport, and then choose from a variety of places to stay that will deliver the luxury you want. Amenities are important when you plan a trip, so we make it easy to find what you want to make your stay special. If you want an upscale hotel with a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Chesapeake has to offer. During your visit, you might want to enjoy the beaches and shopping which Chesapeake is known for.

When can I expect good weather in Chesapeake?

Planning for the weather is an important factor for making your trip to Chesapeake a success, especially when you're splurging. The hottest months are usually July and August with an average temp of 77°F, while the coldest months are January and February with an average of 45°F. Average annual precipitation for Chesapeake is 54 inches.

What's there to see and do in Chesapeake?

Enjoy Chesapeake and visit Greenbrier Mall, Chesapeake Conference Center, and Chesapeake Square Mall. If you have extra time while you're in the area, you might want to stop by Lake Drummond and Chesapeake Arboretum.

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Change your mind

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Check availability on Chesapeake Luxury Hotels

Our top choices for Chesapeake luxury hotels

The Historic Cavalier Hotel and Beach Club, Autograph Collection