Chesapeake City Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Chesapeake City
Great Wolf Lodge Perryville
1240 Chesapeke Overlook Parkway Perryville MD
S$256
31 Aug - 1 Sept
includes taxes & fees
8.8/10 Excellent! (290 reviews)
"Great water park for your family. Bathrooms can be a little bit more clean. Overall excellent location."
Reviewed on 10 Aug, 2026
Quality Inn Newark - Wilmington
65 Geoffrey Dr Newark DE
Fully refundable
S$101
31 Aug - 1 Sept
includes taxes & fees
6/10 (1,017 reviews)
"Nice location"
Reviewed on 10 Aug, 2026
Sonesta Select Newark Christiana Mall
48 Geoffrey Dr Newark DE
Fully refundableReserve now, pay when you stay
S$131
19 Aug - 20 Aug
includes taxes & fees
7.6/10 Good! (1,305 reviews)
"This is not a good place to stay"
Reviewed on 11 Aug, 2026
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.
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.
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 savour local cuisine with views of passing vessels.
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 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
