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Check availability on Chesapeake Luxury Hotels

This weekend
Jun 5 - Jun 7
Next weekend
Jun 12 - Jun 14

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, (1,002 reviews)
  • cleanliness
    Luxurious Virginia Beach retreat offers colonial charm, full-service spa, resort pools, and elegant gardens.
The price is ￥24,798
￥28,839 total
includes taxes & fees
Jun 21 - Jun 22
The Founders Inn and Spa, Tapestry Collection by Hilton
Lobby

The Westin Virginia Beach Town Center

The Westin Virginia Beach Town Center
4.0 star property
Northwest
8.8 out of 10, Excellent, (1,001 reviews)
The price is ￥29,786
￥34,574 total
includes taxes & fees
Jun 14 - Jun 15
The Westin Virginia Beach Town Center
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, (1,002 reviews)
The price is ￥27,423
￥32,016 total
includes taxes & fees
Jun 17 - Jun 18
DoubleTree by Hilton Virginia Beach
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, (1,472 reviews)
The price is ￥33,442
￥38,778 total
includes taxes & fees
Jun 14 - Jun 15
Delta Hotels by Marriott Virginia Beach Waterfront Suites
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, (1,013 reviews)
The price is ￥32,674
￥37,894 total
includes taxes & fees
Jul 6 - Jul 7
DoubleTree by Hilton Virginia Beach Oceanfront South
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, (108 reviews)
The price is ￥41,633
￥48,358 total
includes taxes & fees
Jun 8 - Jun 9
The Inn at Four Eleven York
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, (1,199 reviews)
The price is ￥46,477
￥53,930 total
includes taxes & fees
Jun 15 - Jun 16
Hilton Virginia Beach Oceanfront
Indoor pool, outdoor pool, open 7:00 AM to 11:00 PM, pool umbrellas

Marriott Virginia Beach Oceanfront Resort

Marriott Virginia Beach Oceanfront Resort
4.0 star property
Northeast Virginia Beach
9.0 out of 10, Wonderful, (1,012 reviews)
The price is ￥46,243
￥58,994 total
includes taxes & fees
Jun 14 - Jun 15
Marriott Virginia Beach Oceanfront Resort
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, (1,002 reviews)
  • cleanliness
    Riverside retreat offers rooftop terrace, 3 restaurants, and refined pool in Norfolk's cultural heart.
The price is ￥39,231
￥46,183 total
includes taxes & fees
Jun 24 - Jun 25
Hilton Norfolk The Main
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, (383 reviews)
The price is ￥76,645
￥97,998 total
includes taxes & fees
Jun 17 - Jun 18
The Historic Cavalier Hotel and Beach Club, Autograph Collection
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

6/10 Okay
"The staff was very kind and helpful. We had an experience last year with a smart Alec at the check-in desk, but we did not see him this year. We have stayed at this location many times and will continue to stay here. The location is mostly quiet or as quiet as can be on the oceanfront which is one of the reasons we stay at this location. Most restaurants we prefer are within a 15 minute drive and Waterman’s restaurant is only 2 blocks away, great walk on boardwalk. My only comment may be the suggestion of adding more handicap parking spots and enforce the rules on those who miss use them."
Kimberly 5-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 Lake Drummond and Chesapeake Arboretum.