Chesapeake City Holidays
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Top Flight + Hotel Deals in Chesapeake City
Price found within the past 48 hours. Click for updated prices.
Lord Baltimore Hotel
Downtown Baltimore
€1,043
per person
10 Oct - 15 Oct
found 8 hours ago
Return direct flight included
Athens (ATH) to Baltimore (BWI)
8.4/10 Very good! (3,242 reviews)
It was an experience for sure!! The history of the building is what makes it fun!! The location is scary if traveling after dark. And it’s not as updated as other hotels. But I had a great time!! I have no complaints!! First time staying in a hotel with so much character and lore
Reviewed on 25 Aug 2026
Renaissance Baltimore Harborplace Hotel
Inner Harbor
€1,133
per person
10 Oct - 15 Oct
found 11 hours ago
Return direct flight included
Athens (ATH) to Baltimore (BWI)
8.4/10 Very good! (2,525 reviews)
We found this property clean and conveniently located near the harbor. The front staff was very helpful and accommodating.
Reviewed on 25 Aug 2026
Top hotels in Chesapeake City
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 29 Jun 2026
Great Wolf Lodge Perryville
1240 Chesapeke Overlook Parkway Perryville MD
€176
31 Aug - 1 Sept
includes taxes & fees
8.6/10 Excellent! (314 reviews)
"Let me start with i made this reservation about 2 months in advance and when we got to the hotel the front desk told me our room was. Not ready and we we tired and want to put our stuff in the room after waiting more than 1 hour i got a text saying our room was finally ready which there was no soap ..."
Reviewed on 25 Aug 2026
Quality Inn Newark - Wilmington
65 Geoffrey Dr Newark DE
Fully refundable
€71
2 Sept - 3 Sept
includes taxes & 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.
Stay 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.
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.
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.
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.
Ferryslip Road Park
This waterside park in Chesapeake City offers a tranquil retreat for wildlife watching and peaceful contemplation. Bring a picnic basket and enjoy the serene views where locals gather away from tourist crowds.
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.
Cecil County Public Library Chesapeake City Branch
This community library offers a welcoming space filled with books, digital media, and free Wi-Fi for locals and visitors alike. Browse the diverse collection or join one of their seasonal programmes.
Frequently asked questions
How much does a Chesapeake City holiday package cost?
You'll find cheap prices from €1,003 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 holiday to Chesapeake City costs.
What are the cheapest months to go to Chesapeake City?
If you're looking to snag a cheap Chesapeake City holiday package, consider travelling in April, June and October. You'll typically find lower prices on airfares and hotels during these quieter months — perfect for a budget-friendly break.
How many days is enough for Chesapeake City?
The ideal length for your Chesapeake City holiday depends on what you'd like to see. Usually, a handful of days to a week will give you enough time to check out all the major sights and discover some hidden gems 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 holiday package as soon as possible.
Is it cheaper to book a Chesapeake City holiday as a package?
An Expedia holiday 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 holiday package to Chesapeake City?
If you've got your Chesapeake City holiday 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.
How to plan a trip to Chesapeake City?
- Choose the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to go to Chesapeake City.
- Plan your budget wisely: In addition to the cost of your accommodation, you should factor in other expenses too. These include transportation, food and flights. Also, set aside a little extra for unexpected costs that may come up during your trip to Chesapeake City.
- Work out your trip length: Consider how long you want to spend exploring Chesapeake City. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a comfortable pace.
- Combine your accommodation and airfare: After you've nailed down your dates and duration, lock in the ideal Chesapeake City holiday package for you.
Explore a world of travel with Expedia
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- American Visionary Art Museum
- Visit Cedonia
- Baltimore City Hall
- Baltimore Inner Harbor Marina
- Visit O'Donnell Heights
- Baltimore Holidays
- Belcamp Holidays
- Visit Belcamp
- Bingo World
- Boordy Vineyards
- C and D Canal Museum
- Chesapeake Bay Bridge
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- Visit Colora
- Visit Crumpton
- Dundalk Holidays
- Visit Earleville
- Visit Essex
- Freestate Gun Range
- Garfield Center for the Arts at the Prince Theater
- Greater Baltimore Medical Center
- Greystone Golf Course
- Hammond-Harwood House
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- Korean War Memorial
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- Maryland Zoo
- Monkton Railroad Station
- Morgan State University
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- Patterson Park
- Sandy Point State Park
- Star-Spangled Banner Flag House
- Walters Art Museum
- Visit Worton
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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.
