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

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Check availability on Chesapeake Luxury Hotels

Tonight
3 Oct - 4 Oct
Tomorrow
4 Oct - 5 Oct
Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct

Our top choices for Chesapeake luxury hotels

1. Hilton Norfolk The Main

Hilton Norfolk The Main
Downtown Norfolk
  • Riverside retreat offers rooftop terrace, 3 restaurants, and refined pool in Norfolk's cultural heart.
£226
includes taxes & fees
12 Oct - 13 Oct
Hilton Norfolk The Main

2. The Inn at Four Eleven York

The Inn at Four Eleven York
West Freemason
£205
includes taxes & fees
5 Oct - 6 Oct
The Inn at Four Eleven York
View all properties

Find out more about Chesapeake

Chesapeakeand its attractions for luxury travelers

Chesapeake, Virginia, offers a range of experiences that cater perfectly to luxury travellers seeking both adventure and relaxation. Begin your journey at the Great Dismal Swamp National Wildlife Refuge, where you can enjoy guided eco-tours aboard a private boat, exploring the tranquil waterways and spotting unique wildlife. For a taste of culture, visit the Chesapeake City Park, which not only boasts beautiful walking trails but also features the impressive Chesapeake Planetarium for an out-of-this-world experience in stargazing. If you’re a golf enthusiast, the Riverfront Golf Club is a must-visit, where you can tee off on a meticulously designed course, followed by a sumptuous meal at the clubhouse overlooking the pristine greens. Families will appreciate the nearby Children's Museum of Virginia, where interactive exhibits ensure that even the youngest members of your party can indulge in creative fun. When it comes to accommodation, the Greenbrier is known for its luxurious amenities and exceptional service, perfectly situated to allow easy access to these attractions. After a day of exploring, unwind at the hotel's lavish spa, where you can experience bespoke treatments tailored to your needs, ensuring your stay is both comfortable and indulgent.

Top Chesapeake Hotel Reviews

Schooner Inn

Schooner Inn

10/10 Excellent
"This place never disappoints. Everything was clean, always a plus having a kitchenette while on vacation. You can't beat the location and the oceanview. Staff was welcoming and very helpful. Overall excellent place to stay."
Brandon 3-night trip
Posted 16 hours ago
Schooner Inn
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

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

10/10 Excellent
"I am in VA Beach once every September for the air show but I do not have a go-to place. I do try to stay on the beach searching by price and amenities. I really enjoyed my stay and the greatest compliment I can give is that I plan to stay here again next September."
Shawn 3-night trip
Posted 18 hours ago
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)
Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk

8/10 Good
"It was good experience."
Jimmy 1-night trip
Posted 1 day ago
Comfort Suites Chesapeake - Norfolk
Hilton Virginia Beach Oceanfront

Hilton Virginia Beach Oceanfront

10/10 Excellent
"Staff is fantastic and location could not be better. We enjoyed dinner at Catch 31, excellent. We loved the fire pits outside and rocking chairs. Perfect set up for a beach trip!"
Victoria 1-night trip
Posted 2 days ago
Hilton Virginia Beach Oceanfront

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, VA (ORF-Norfolk Intl.) airport or Newport News, VA (PHF-Newport News - Williamsburg Intl.) 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 get what you'd like to make your stay special. If you want an upscale hotel with fine dining, a spa or several swimming pools, Expedia can assist you in finding the best luxury hotel experience that Chesapeake offers. 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 temperature of 25°C, while the coldest months are January and February, with an average of 7°C. Average annual precipitation for Chesapeake is 1359 mm.
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.

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