Chesapeake City Vacations from $255

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Your Chesapeake City Vacation

The vibrant city of Chesapeake City is calling your name. Discover its hot spots and hidden treasures with a Chesapeake City vacation package that's customized to you. Bohemia Vista Marina, C and D Canal Museum and East Meadow Park are just some of the many attractions you'll want to check out during your trip to Chesapeake City. Expedia is here to help you escape your routine. Tailor your vacation to Chesapeake City to match your travel style, whatever that may look like.

The Latest Chesapeake City vacation packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Hotel Laurel
Graduate by Hilton Annapolis
Pier 5 Hotel Baltimore
Historic Inns of Annapolis
Hotel Ulysses, a Member of Design Hotels
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Chesapeake City Hotel Deals

Historic Chesapeake City Stay

Historic Chesapeake City Stay

Chesapeake City
$263 nightly
The price is $279 total per night from Oct 6 to Oct 7
$279 total
Oct 6 - Oct 7
Total with taxes and fees
9/10 Wonderful! (16 reviews)
"house was clean and ready for us. It is perfect for two people in a quiet neighborhood. Had a little trouble with the electronic door lock because of low battery but it was reconciled very promptly."

Reviewed on Sep 21, 2025

Historic Chesapeake City Stay
Sonesta Select Newark Christiana Mall

Sonesta Select Newark Christiana Mall

3 out of 5
48 Geoffrey Dr, Newark, DE
Fully refundableReserve now, pay when you stay
$117 nightly
The price is $130 total per night from Oct 7 to Oct 8
$130 total
Oct 7 - Oct 8
Total with taxes and fees
7.6/10 Good! (1,117 reviews)
"Great stay"

Reviewed on Oct 1, 2025

Sonesta Select Newark Christiana Mall
Embassy Suites by Hilton Newark Wilmington South

Embassy Suites by Hilton Newark Wilmington South

3.5 out of 5
654 S College Ave, Newark, DE
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $126 total per night from Nov 2 to Nov 3
$126 total
Nov 2 - Nov 3
Total with taxes and fees
8/10 Very Good! (1,030 reviews)
"x"

Reviewed on Sep 29, 2025

Embassy Suites by Hilton Newark Wilmington South
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.

Chesapeake City Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Wilmington, DE (ILG-New Castle)
Population
690
Max Temp Winter
40ºF
Max Temp Summer
85ºF
Top Sights
Elk Neck State Park, Historical Society of Cecil County and Milburn Stone Theater

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Frequently asked questions

How much does a Chesapeake City vacation package cost?
You'll find cheap prices from $255 on Expedia for your Chesapeake City getaway. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to Chesapeake City costs.
What are the cheapest months to go to Chesapeake City?
November, December and January are great times to look for cheap Chesapeake City vacation packages. Traveling in less busy months means you'll typically find lower prices on accommodations and flights.
How many days is enough for Chesapeake City?
The ideal length for your Chesapeake City vacation depends on what you'd like to do. Usually, a handful of days to a week will give you enough time to go to all the leading sights and explore some hidden treasures along the way.
How to find the best Chesapeake City package deals?
Use Expedia's filters to find some unbeatable Chesapeake City package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Chesapeake City package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Chesapeake City vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging stays and flights separately. Better still, you can tailor your Chesapeake City trip to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Chesapeake City?
If you've got your Chesapeake City vacation dates locked in, book as early as you can to grab some unbeatable deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are perfect for quick escapes.
Does Expedia offer Book Now, Pay Later Chesapeake City vacation packages?
Secure your dream escape to Chesapeake City with help from our Book Now, Pay Later vacations. No need to save like crazy or hold off until payday — we've partnered with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans mean you can split the cost over 3, 6 or 12 months. With no late payment fees or extra charges, you can easily stay on budget and snap up travel deals before they disappear.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.