Chesapeake City Vacations from $279
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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.
The LINE Hotel DC
Northwest
$416
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.6/10 Excellent! (1,003 reviews)
Be aware that valet parking is twice as advertised Taxes and fees are more than parking itself.
Reviewed on Aug 9, 2026
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View all tripsStay near popular Chesapeake City attractions
Chesapeake Inn Marina
Explore the waterfront in Chesapeake City with a trip to Chesapeake Inn Marina. Stroll along the marina or experience the area's museums.
C and D Canal Museum
8.0/10 (3 reviews)
Housed in an 1837 pump house, the C&D Canal Museum showcases the engineering marvel that transformed regional shipping. View original steam engines and interactive exhibits bringing 19th-century canal operations to life.
Chesapeake City Park
Chesapeake City Park is just one of the places to see in Chesapeake City, so why not enjoy the other things to explore during your travels? Stroll along the marina or experience the area's museums.
Chesapeake City Docks
Explore the waterfront in Chesapeake City with a trip to Chesapeake City Docks. Amble around the area's marina or experience its museums.
Bohemia Bay Yacht Harbour
Explore the waterfront in Chesapeake City with a trip to Bohemia Bay Yacht Harbour. Amble around the area's marina or experience its museums.
Two Rivers Yacht Basin
Explore the waterfront in Chesapeake City with a trip to Two Rivers Yacht Basin. Stroll along the marina or experience the area's museums.
South Chesapeake City Historic District
Stroll through this canal-side district where 19th-century Greek Revival and Italianate buildings tell stories of maritime prosperity. Browse waterfront boutiques and savor local cuisine with views of passing vessels.
The Pell Gardens
This charming waterfront park offers tranquil views of boats navigating the Chesapeake & Delaware Canal. Relax in the gazebo or stroll the flower-lined paths while soaking in the maritime atmosphere.
Chesapeake City Hotel Deals
HYDRANGEA HOUSE Waterview cozy 3-bdrm Getaway in quiet Chesapeake City AC & yard
Chesapeake City MD
10/10 Exceptional! (1 review)
"Cute place, great location!The owner told us we were the first booking since she purchased the home! It was perfect for my stay, located right by the C&D Canal, the Recreation Trail (and the bike rentals were right there!) and we walked to Schaefer’s for a sunset cocktail. I had some questions for ..."
Reviewed on Jun 29, 2026
Great Wolf Lodge Perryville
1240 Chesapeke Overlook Parkway Perryville MD
$179 nightly
$200 total
Aug 31 - Sep 1
Total with taxes and fees
8.8/10 Excellent! (288 reviews)
"Clean and great place to stay."
Reviewed on Aug 8, 2026
Quality Inn Newark - Wilmington
65 Geoffrey Dr Newark DE
Fully refundable
$67 nightly
$75 total
Sep 7 - Sep 8
Total with taxes and fees
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.
Find the Best Chesapeake City Vacation Packages
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 $279 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
