Chesapeake City Vacation Packages
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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.
Top Chesapeake City Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Furnished Apartments
Ashton Heights
CA $824
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9/10 Wonderful! (4 reviews)
Location is excellent. Walking distance to pretty much everything you need. Space was very comfortable, clean, and the bed was excellent for sleeping. Lots of light and windows.
Host was helpful and able to accommodate my schedule needs too.
Reviewed on Apr 1, 2025
Ready to book your vacation to Chesapeake City?
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
CA $250
CA $279 total
Sep 1 - Sep 2
includes taxes & fees
8.6/10 Excellent! (287 reviews)
"The hotel is nice, they do many activities I thought it was great the previous ones a little expensive and the cleanliness I give it a 4, in general I recommend them"
Reviewed on Aug 6, 2026
Quality Inn Newark - Wilmington
65 Geoffrey Dr Newark DE
Fully refundable
CA $93
CA $103 total
Sep 8 - Sep 9
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.
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.
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 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
Learn about the local history of Chesapeake City when you spend time at South Chesapeake City Historic District. 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 $688 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.
