Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Search 321,000 hotels worldwide.

Get the price guarantee available for your trip.

No Expedia cancellation fee to change or cancel almost any hotel reservation.


Featured Chesapeake Luxury Hotels

See all 614 Hotels in Chesapeake
Hyatt Place Chesapeake

Hyatt Place Chesapeake

709 Eden Way N, Chesapeake
3.0 out of 5.0
4.4 out of 5 (217 reviews)
The rooms are very contemporary. and are very relaxing
  Sep 20, 2017

$94

$94
InTown Suites- Chesapeake I-64

InTown Suites- Chesapeake I-64

1520 Crossways Blvd, Chesapeake
2.0 out of 5.0
2.7 out of 5 (202 reviews)
Great location to Norfolk and Virginia BeachThis location is near a lot of shopping, movies, restaurants, and less than 30 minutes to Norfolk or Virginia Beach. The cost was very reasonable. The manager and staff were very nice. I liked having a kitchenette. The unit was reasonably clean...I only used one Clorox wipe to disinfect all surfaces ...
  Jul 9, 2015
Aloft Chesapeake

Aloft Chesapeake

1454 Crossways Boulevard, Chesapeake
3.0 out of 5.0
4.1 out of 5 (294 reviews)
Friendly staff, very clean and modern. Plenty of amenities and food!
  Sep 12, 2017

$99

$99
Red Roof Inn Chesapeake Conference Center

Red Roof Inn Chesapeake Conference Center

724 Woodlake Dr, Chesapeake
2.0 out of 5.0
3.2 out of 5 (213 reviews)
Great stayDidn't expect much being it was the Red Roof but it was Awesome. Mrs. Sandra, the young lady at the check in desk was so sweet and awesome getting me and hubby checked in. It was a sold out weekend and she was extremely busy but she was still kind and professional. The room was better than expected ...
  Sep 17, 2017

$46

$46
Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake

817 Greenbrier Circle, Chesapeake
2.5 out of 5.0
3.9 out of 5 (23 reviews)
Very Satisfying Stay!Staff was friendly, very pleasant. Loved the feel of the hotel..cozy, warm and clean. Hotel is tucked into a nice area. Quiet, away from the freeway. Very close to a great choice of reatauarants and a mall.
  Sep 11, 2017

$73

$73
Courtyard by Marriott Chesapeake

Courtyard by Marriott Chesapeake

1562 Crossways Blvd, Chesapeake
3.0 out of 5.0
3.9 out of 5 (60 reviews)
It worked for the trip but the room was pricey compared to other courtyards so price wise I would not consider this hotel. Price and quality of the hotel did not match up
  Aug 17, 2017

$127

$127
Map

Recently booked Luxury Hotels in Chesapeake

Marriott Chesapeake
3.5 out of 5.0
Last booking: 1 hour ago
Red Roof Inn Chesapeake Conference Center
2.0 out of 5.0
Last booking: 2 hours ago
WoodSpring Suites Chesapeake-Norfolk Greenbrier
2.0 out of 5.0
Last booking: 4 hours ago
Aloft Chesapeake
3.0 out of 5.0
Last booking: 5 hours ago
Staybridge Suites Chesapeake
3.0 out of 5.0
Last booking: 5 hours ago
Wingate by Wyndham Chesapeake
2.5 out of 5.0
Last booking: 5 hours ago
Extended Stay America - Chesapeake - Churchland Blvd.
2.5 out of 5.0
Last booking: 7 hours ago
Studios and Suites 4 Less
1.5 out of 5.0
Last booking: 7 hours ago
Days Inn Chesapeake Portsmouth
2.0 out of 5.0
Last booking: 9 hours ago

A few days away keeps your worries at bay, especially when you're visiting Chesapeake. Fascinating points of interest, scrumptious eats, and opportunities to capture phenomenal photos: these are just a few of the benefits of visiting Chesapeake. You'll snag seats to the most popular performances, devour fabulous eats, and get in line to check out the coolest points of interest. Naturally, you'll stay at a luxury hotel! Extravagant experiences are right up your alley, so get your upscale hotel in Chesapeake on Expedia.com right now and start your excursion off on the right (well-dressed) foot.

Book a Luxury Chesapeake Vacation

It turns out plenty of folks love Chesapeake enough to live here -- how is that for proof that Chesapeake is full of wonderful things to do? No matter what brings you to Chesapeake, the destination always delivers. Chesapeake is full of impressive hotels on top of appealing attractions, so you can count on a remarkable stay. Crowds have doubled in the last year, so book early!

Your luxury vacation is the perfect opportunity to indulge in art, culture, and spa treatments. When you book your trip on Expedia.com, you never have to limit yourself. Thanks to our hotel deals, you'll still have enough money for the most fun and free-spirited things to do. After an eventful day of exploration, your luxury accommodation awaits. Before you go to bed, order a glass of wine to your room and reflect on your day of enriching experiences. The luxury hotels in Chesapeake will soothe you into a state of serenity as soon as you check in.

Find Luxury Chesapeake Hotels Now

It's that time; you're prepared to get swept away in Chesapeake, and Expedia.com is here to make the process painless. Browse the bounty of real traveler reviews on incredible hotels to find an accommodation that suits your needs. 5-Star hotels treat you right, offering things like concierge services and private kitchens. Many luxe accommodations in Chesapeake even feature gigantic suites, and it's not uncommon to enjoy incredible in-house dining in your hotel. Use our mobile booking app to find and book a fabulous 5-star hotel in Chesapeake, and soon you'll be soaking up luxury in style!