Title: 5 Stars Hotels in Chesapeake City, Maryland from CA $158 - Find Cheap Chesapeake City Hotels With 5 Stars | Expedia.ca

[Chesapeake City Travel Guide](https://expedia.ca/Chesapeake-City.dx177517)[Hotels in Chesapeake City](https://expedia.ca/Chesapeake-City-Hotels.d177517.Travel-Guide-Hotels)[Vacation Rentals in Chesapeake City](https://expedia.ca/Chesapeake-City-Vacation-Rentals.d177517.Travel-Guide-VacationRentals)[Flights to Chesapeake City](https://expedia.ca/Cheap-Flights-To-Chesapeake-City.d177517.Travel-Guide-Flights)[Things to do in Chesapeake City](https://expedia.ca/Things-To-Do-In-Chesapeake-City.d177517.Travel-Guide-Activities)[Chesapeake City Car Rentals](https://expedia.ca/Car-Rentals-In-Chesapeake-City.d177517.Car-Rental-Guide)[Chesapeake City Vacation Packages](https://expedia.ca/Chesapeake-City.d177517.Destination-Travel-Guides)

![An aerial view of historic Annapolis, situated on the Chesapeake Bay, during an early November morning.](https://images.trvl-media.com/place/177517/30c1fc19-3278-4d8b-9ab8-b49b3730e600.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check availability on Chesapeake City 5 Star Hotels

Tonight

[Jan 30 - Jan 31](https://www.expedia.ca/Hotel-Search?regionId=177517&startDate=2026-01-30&endDate=2026-01-31&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

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[Jan 31 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=177517&startDate=2026-01-31&endDate=2026-02-01&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

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[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=177517&startDate=2026-01-30&endDate=2026-02-01&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

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[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=177517&startDate=2026-02-06&endDate=2026-02-08&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

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## Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Chesapeake City.

![Hilton Wilmington/Christiana](https://images.trvl-media.com/lodging/1000000/10000/7100/7053/7640fa86_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Hilton Wilmington/Christiana

100 Continental Dr Newark DE

CA $143

CA $158 total

Feb 28 - Mar 1

includes taxes & fees

8.8/10 Excellent! (1,005 reviews)

[](https://expedia.ca/Wilmington-Hotels-Hilton-WilmingtonChristiana.h7053.Hotel-Information)

![The Westin Wilmington](https://images.trvl-media.com/lodging/8000000/7420000/7415800/7415754/251369d9_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### The Westin Wilmington

818 Shipyard Drive Wilmington DE

CA $266

CA $292 total

Feb 14 - Feb 15

includes taxes & fees

8.6/10 Excellent! (855 reviews)

[](https://expedia.ca/Wilmington-Hotels-The-Westin-Wilmington.h7415754.Hotel-Information)

Still don't see what you're looking for?

[See all properties in Chesapeake City.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=01%2F02%2F2026&endDate=02%2F02%2F2026&regionId=177517&star=50)

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[Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=01%2F02%2F2026&endDate=02%2F02%2F2026&regionId=177517&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=01%2F02%2F2026&endDate=02%2F02%2F2026&regionId=177517&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=01%2F02%2F2026&endDate=02%2F02%2F2026&regionId=177517&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=01%2F02%2F2026&endDate=02%2F02%2F2026&regionId=177517&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=01%2F02%2F2026&endDate=02%2F02%2F2026&regionId=177517&star=50&star=50&amenities=WATER_PARK)

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.

## Learn more about Chesapeake City

This charming canal town offers waterfront dining where you can watch massive ships pass surprisingly close to shore. Explore the C&D Canal Museum to understand Chesapeake City's maritime history, then stroll across the bridge for spectacular views at sunset.

[See all hotels in Chesapeake City](https://www.expedia.ca/Hotel-Search?startDate=2026-02-14&endDate=2026-02-15&adults=2&regionId=177517)

![An aerial view of historic Annapolis, situated on the Chesapeake Bay, during an early November morning.](https://images.trvl-media.com/place/177517/30c1fc19-3278-4d8b-9ab8-b49b3730e600.jpg?impolicy=fcrop&w=900&h=666&p=1&q=high)

## Top Chesapeake City Hotel Reviews

## Find out more about Chesapeake City

## Five Star Hotels in Chesapeake City

There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Chesapeake City so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Chesapeake City and get ready to be pampered like never before.

#### Get a Great Deal on 5-Star Hotels in Chesapeake City

Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places. 

Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town.

#### Make Your Escape to Chesapeake City

The results are in, and Chesapeake City 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Chesapeake City! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Chesapeake City today and settle down in the lap of luxury tomorrow.

## Frequently asked questions

### How much does it cost to stay in a 5-star hotel in Chesapeake City?

> - Search for the lowest price per night from CA $158

### What makes a hotel 5 stars in Chesapeake City?

### Are there any 5-star all-inclusive resorts in Chesapeake City?

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