Find 5 Star Hotels in Chesapeake City, MD from $96

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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

Hilton Wilmington/Christiana

100 Continental Dr Newark DE
$87 nightly
The price is $96 total per night from Jan 10 to Jan 11
$96 total
Jan 10 - Jan 11, 2026
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
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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.

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An aerial view of historic Annapolis, situated on the Chesapeake Bay, during an early November morning.

Top Chesapeake City Hotel Reviews

Find out more about Chesapeake City

Ready to experience the next standard in luxury? We know you're thinking about it. Add further pleasure on your next trip to Chesapeake City by treating yourself to the best of the best when it comes to accommodation. It's an ideal combination. There's no reason to delay a getaway to Chesapeake City any longer. You'll join the multitudes of vacationers who have made Chesapeake City so fashionable recently. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Don't wait any longer. Our 5-star hotels in Chesapeake City are the perfect places to relax in during your next chunk of time off.

5-Star Hotels in Chesapeake City

You'll have a fantastic time at one of these 5-star hotels. High-end restaurants, concierges, and in-room spa sessions are all at the ready. You're sure to find exactly the accommodation you need. You'll also enjoy a high standard of care and meticulous guest relations, so get ready to kick back and indulge. How do you want to relax? A full-body massage to help your cares fall away? A concierge to help you make reservations at that outstanding restaurant? Plush carpeting, piping hot coffees, and even a hot tub in the bathroom...these hotels will astonish you. Want to see for yourself? Explore our listings and pick the perfect accommodation for your needs.

You won't sleep and order room service the entire time, though. You're in luck. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what you end up doing, the 5-star hotels in Chesapeake City are the perfect place to rest up after a busy day.

Your Getaway Starts Today

The results are in, and Chesapeake City 5-star hotels are the place to be when you book your next vacation. If you've been dreaming about a vacation set here, then go ahead and book it. It's time to indulge yourself -- Expedia can help you land a great deal on accommodation. Decide on one of our Chesapeake City 5-star hotels today and settle down in luxe surroundings tomorrow.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Chesapeake City?
The amount you pay for a 5-star hotel in Chesapeake City depends on things like when you plan to go and the length of your vacation. Our top tip for bagging the best deal? Use our pricing filters to check out the available options for your chosen dates.

  • Search for the lowest price per night from $96

What makes a hotel 5 stars in Chesapeake City?
In Chesapeake City, a hotel must provide a certain amount of high-end amenities to earn 5 stars. These can include on-site gyms, gourmet restaurants, saunas and spas, premium bedding, luxury toiletries and more. What also sets 5-star hotels apart is their extraordinary standard of service. You'll enjoy things like in-room massages, nightly turn-down services and concierge services. Some may also offer extra touches like a welcome gift.
Are there any 5-star all-inclusive resorts in Chesapeake City?
Find a luxurious stay that includes your room, meals, activities and entertainment in Chesapeake City with the help of Expedia's filters. Search for resorts with a 5-star rating and click on the "All inclusive" filter. Be sure to check what's included in the upfront price. This way, you can take full advantage of the premium perks on offer when you get there.

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