A golf course, a large building complex, and a marina by a river.

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Check availability on Chesapeake Luxury Hotels

Our top choices for Chesapeake luxury hotels

A modern interior with a black leather sofa, green and yellow chairs, and a patterned floor.

1. Hilton Norfolk The Main

Hilton Norfolk The Main
4.0 star property
Downtown Norfolk
9.0 out of 10, Wonderful, (1,003 reviews)
  • cleanliness
    Riverside retreat offers rooftop terrace, 3 restaurants, and refined pool in Norfolk's cultural heart.
The price is ￥29,730
￥35,116 total
includes taxes & fees
Nov 22 - Nov 23
Hilton Norfolk The Main
A dining area with a wooden table and chairs, a chandelier, and a view into a room with a fireplace.

2. The Inn at Four Eleven York

The Inn at Four Eleven York
4.0 star property
West Freemason
10.0 out of 10, Exceptional, (117 reviews)
The price is ￥39,650
￥46,076 total
includes taxes & fees
Dec 16 - Dec 17
The Inn at Four Eleven York
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.
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Top Chesapeake Hotel Reviews

Schooner Inn

Schooner Inn

10/10 Excellent
"Great!"
Leigh-Ann 3-night trip
Posted less than an hour ago
Schooner Inn

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 Chesapeake Veterans' Memorial and Northwest River Park and Campground.