Colorful sunset over riverside resort in Cambridge Maryland USA

Find Luxury Hotels in Chesapeake, VA

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chesapeake Luxury Hotels

Our top choices for Chesapeake luxury hotels

Courtyard

The Founders Inn and Spa, Tapestry Collection by Hilton

The Founders Inn and Spa, Tapestry Collection by Hilton
4.0 star property
Virginia Beach
8.4 out of 10, Very Good, (1,004 reviews)
  • cleanliness
    Luxurious Virginia Beach retreat offers colonial charm, full-service spa, resort pools, and elegant gardens.
The price is ￥24,882
￥28,933 total
includes taxes & fees
Jun 22 - Jun 23
The Founders Inn and Spa, Tapestry Collection by Hilton
Lobby

DoubleTree by Hilton Virginia Beach

DoubleTree by Hilton Virginia Beach
4.0 star property
Northeast Virginia Beach
8.2 out of 10, Very Good, (1,001 reviews)
The price is ￥27,515
￥32,124 total
includes taxes & fees
Jun 17 - Jun 18
DoubleTree by Hilton Virginia Beach
Lobby

The Westin Virginia Beach Town Center

The Westin Virginia Beach Town Center
4.0 star property
Northwest
8.8 out of 10, Excellent, (1,002 reviews)
The price is ￥27,157
￥31,553 total
includes taxes & fees
Jun 28 - Jun 29
The Westin Virginia Beach Town Center
Breakfast, lunch and dinner served

DoubleTree by Hilton Virginia Beach Oceanfront South

DoubleTree by Hilton Virginia Beach Oceanfront South
4.0 star property
Northeast Virginia Beach
8.2 out of 10, Very Good, (1,019 reviews)
The price is ￥30,207
￥35,059 total
includes taxes & fees
Jun 16 - Jun 17
DoubleTree by Hilton Virginia Beach Oceanfront South
Bar (on property)

Delta Hotels by Marriott Virginia Beach Waterfront Suites

Delta Hotels by Marriott Virginia Beach Waterfront Suites
4.0 star property
Northeast Virginia Beach
8.4 out of 10, Very Good, (1,482 reviews)
The price is ￥48,004
￥55,526 total
includes taxes & fees
Jun 28 - Jun 29
Delta Hotels by Marriott Virginia Beach Waterfront Suites
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

Hilton Virginia Beach Oceanfront

Hilton Virginia Beach Oceanfront
4.0 star property
Northeast Virginia Beach
8.6 out of 10, Excellent, (1,204 reviews)
The price is ￥49,610
￥57,371 total
includes taxes & fees
Jun 16 - Jun 17
Hilton Virginia Beach Oceanfront
3 restaurants; breakfast, lunch, dinner, and brunch served

Hilton Norfolk The Main

Hilton Norfolk The Main
4.0 star property
Downtown Norfolk
9.0 out of 10, Wonderful, (1,009 reviews)
  • cleanliness
    Riverside retreat offers rooftop terrace, 3 restaurants, and refined pool in Norfolk's cultural heart.
The price is ￥39,364
￥46,341 total
includes taxes & fees
Jun 24 - Jun 25
Hilton Norfolk The Main
Front of property

The Inn at Four Eleven York

The Inn at Four Eleven York
4.0 star property
West Freemason
10.0 out of 10, Exceptional, (109 reviews)
The price is ￥44,501
￥51,657 total
includes taxes & fees
Jun 14 - Jun 15
The Inn at Four Eleven York
Indoor pool, seasonal outdoor pool

The Historic Cavalier Hotel and Beach Club, Autograph Collection

The Historic Cavalier Hotel and Beach Club, Autograph Collection
4.0 star property
Northeast Virginia Beach
9.4 out of 10, Exceptional, (384 reviews)
The price is ￥76,836
￥98,243 total
includes taxes & fees
Jun 22 - Jun 23
The Historic Cavalier Hotel and Beach Club, Autograph Collection
Terrace/patio

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
4.0 star property
Northeast Virginia Beach
8.2 out of 10, Very Good, (1,298 reviews)
The price is ￥33,061
￥47,564 total
includes taxes & fees
Jun 17 - Jun 18
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
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.
View all properties

Top Chesapeake Hotel Reviews

Hilton Virginia Beach Oceanfront

Hilton Virginia Beach Oceanfront

10/10 Excellent
"Clean room, beach view"
Michelle 1-night trip
Posted 2 hours 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 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.