The Best Luxury Hotels in Chesapeake, VA from ￥11,733 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

￥98,170 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.

￥28,839 total

includes taxes & fees

Jun 22 - Jun 23

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

Hilton Virginia Beach Oceanfront

Northeast Virginia Beach

￥54,024 total

includes taxes & fees

Jun 15 - Jun 16

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

Marriott Virginia Beach Oceanfront Resort

Northeast Virginia Beach

￥59,098 total

includes taxes & fees

Jun 14 - Jun 15

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.

￥46,265 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.

￥25,523 total

includes taxes & fees

Jun 29 - Jun 30

The Westin Virginia Beach Town Center

Northwest

￥34,636 total

includes taxes & fees

Jun 14 - Jun 15

Delta Hotels by Marriott Virginia Beach Waterfront Suites

Northeast Virginia Beach

￥38,847 total

includes taxes & fees

Jun 14 - Jun 15

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Top Chesapeake Hotel Reviews

Holiday Inn & Suites Virginia Beach North Beach by IHG

10/10 Excellent

"La pasamos muy bien y todos súper atentos"

Wyndham Virginia Beach Oceanfront

2/10 Terrible

"The location is excellent. Right on the beach, but isolated a little from the rest of the crowded beaches of the reatif virginia beach's resort area. However, checking in with the night crew was a disaster. I had to wait almost thirty mins for Todd to check in the guest before me. Then he checked me into the wrong room and told me that was the only room available. When I finally got to the room the door wouldn't accept the key. Todd then changed my room to a non oceanfront room even though I paid more money for a coastal room. I checked on the Wyndham app and confirmed that there was other options available, then asked Todd to upgrade me. He told me if I wanted an upgrade I would need to book the other room online then request a refund from expedia. So much for hospitality."

Hilton Vacation Club Ocean Beach Club Virginia Beach

10/10 Excellent

"My family and I had an amazing stay at Hilton Vacation Club Ocean Beach Club! This trip was very meaningful to us because we were celebrating both my daughter’s 4th birthday and my graduation weekend, and the experience exceeded our expectations. The resort was clean, comfortable, and in a perfect location right by the beach. The staff was friendly and welcoming, which made our stay even more enjoyable. We loved being able to relax, enjoy being at a walking distance from the beach, and make special memories together as a family. Everything about our stay helped make our celebration weekend feel extra special. My daughter had a wonderful birthday, and I couldn’t have asked for a better place to celebrate such an important milestone in my life. I really enjoyed my time here and can’t wait to come back again in the future. Thank you for helping make our special weekend one to remember!"

The Ocean Key Virginia Beach Resort

8/10 Good

"I stayed for a long weekend with my husband and 3 kids. This place was great for our needs. It's definitely not a luxury hotel by any means, and could use some upgrades. However, it was clean and in a great location. Easy walk to the beach and has an indoor pool my kids loved. You can hear all the cars driving by at night, so if you're sensitive to sounds, this may be a tough spot for you"

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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Our top choices for Chesapeake luxury hotels

The Historic Cavalier Hotel and Beach Club, Autograph Collection