Chesapeake City Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
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.
Top Chesapeake City Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Crowne Plaza Crystal City-Washington, D.C. by IHG
Crystal City
CA $811
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
8.2/10 Very good! (1,002 reviews)
Everything neat spacious clean.
Nice bed soft bathroom clean enough towels and wash cloths overall good stay.
Reviewed on Oct 3, 2026
Ready to book your vacation to Chesapeake City?
Chesapeake City Hotel Deals
Sonesta Select Newark Christiana Mall
48 Geoffrey Dr Newark DE
Fully refundableReserve now, pay when you stay
CA $143
CA $159 total
Oct 22 - Oct 23
includes taxes & fees
7.6/10 Good! (1,289 reviews)
"Had I known the entire first floor was being renovated, I would have selected a different hotel. It was terribly inconvenient and there wasn’t any breakfast in the morning, as is customary for hotels like this. It took three tries for my key card to work when I was checking in and then on my third ..."
Reviewed on Oct 2, 2026
Embassy Suites by Hilton Newark Wilmington South
654 S College Ave Newark DE
Fully refundableReserve now, pay when you stay
CA $151
CA $167 total
Oct 25 - Oct 26
includes taxes & fees
8.6/10 Excellent! (1,019 reviews)
"It was clean ,peaceful and quiet. Good food. Great staff"
Reviewed on Oct 2, 2026
Quality Inn Newark - Wilmington
65 Geoffrey Dr Newark DE
Fully refundable
CA $86
CA $96 total
Nov 1 - Nov 2
includes taxes & fees
6.2/10 (1,003 reviews)
"The room smelled. It’s run down and gross."
Reviewed on Oct 3, 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.
Bohemia Vista Marina
10.0/10 (3 reviews)
Explore the waterfront in Chesapeake City with a trip to Bohemia Vista Marina. While in this family-friendly area, you can savor the top-notch restaurants.
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.
Ferryslip Road Park
After visiting Ferryslip Road Park, make a plan to see the other sights and activities in Chesapeake City. Amble around the area's marina or experience its museums.
C and D Canal Museum
8.0/10 (3 reviews)
You can spend time exploring the galleries in C and D Canal Museum during your trip to Chesapeake City. While you're here, you can savor the top-notch restaurants.
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.
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.
Chesapeake City Town Hall
Chesapeake City Town Hall is just one of the places to see in Chesapeake City, so why not enjoy the other things to explore during your travels? Amble around the area's marina or experience its museums.
Frequently asked questions
How much does a Chesapeake City vacation package cost?
You can grab a vacation package to this popular destination from CA $805 on Expedia. However, how much your vacation to Chesapeake City costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Chesapeake City?
If you'd like to score a cheap Chesapeake City vacation package, consider planning a trip in April, June and October. You'll typically find better rates on airfares and hotels during these months — perfect for budget-conscious travellers.
How many days is enough for Chesapeake City?
You can easily explore all the main attractions in Chesapeake City within a few days, including the must-see Cow Pond. If you're after a longer Chesapeake City vacation, look at what sort of day tours and activities are available in the area.
How to find the best Chesapeake City package deals?
Start your search for a Chesapeake City package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Chesapeake City package deal straight away, simply switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Chesapeake City escape underway.
Is it cheaper to book a Chesapeake City vacation as a package?
You can enjoy significant savings on your Chesapeake City retreat by booking a personalized vacation package. Check the "Package" heading, then enter your travel dates and destination to view some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Chesapeake City?
If you're planning a spontaneous Chesapeake City vacation, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can score amazing deals on your flights and hotels by booking well in advance.
How to plan a trip to Chesapeake City?
- Choose when to travel: Check your calendar and get packing. Your preferred time of year and the type of activities available will also help you decide when to escape to Chesapeake City.
- Calculate your budget: Make sure you have enough money to pay for everything from dining out and transportation to activities and flights. Your hotel will probably be the biggest expense during your trip to Chesapeake City.
- Decide your trip length: Think about how long you'd like to spend exploring Chesapeake City. Plan your days so you can get to all the experiences and attractions you're interested in without rushing.
- Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to choose a Chesapeake City vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
