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.
Tru By Hilton Baltimore Harbor East, MD

Tru By Hilton Baltimore Harbor East, MD

2.5 out of 5
Little Italy
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9.2/10 Wonderful! (1,000 reviews)
Ok. No pool. To far away from convention center

Reviewed on Aug. 3, 2025

Hampton Inn & Suites Baltimore Inner Harbor

Hampton Inn & Suites Baltimore Inner Harbor

2.5 out of 5
Downtown Baltimore
per person
Oct 9 - Oct 13
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.6/10 Excellent! (1,004 reviews)
The staff was amazing and made us feel like family.

Reviewed on Aug. 4, 2025

Hotel Ulysses, a Member of Design Hotels

Hotel Ulysses, a Member of Design Hotels

4 out of 5
Mount Vernon
per person
Oct 9 - Oct 13
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9.2/10 Wonderful! (902 reviews)
The site was very clean and comfortable

Reviewed on Aug. 3, 2025

Baltimore Marriott Inner Harbor at Camden Yards

Baltimore Marriott Inner Harbor at Camden Yards

4 out of 5
Downtown West
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.2/10 Very Good! (1,001 reviews)
Great location to Camen Yards and Inner Harbor. Close to interstate highway to easy to get in and out of town. We were given an handicapped accessible room because it was available at our time of check in which was okay with us and they gave us access to the 10th floor lounge as a thank you. Saved us some $$ on food! All employees very nice - reception, bar, 10th floor lounge.

Reviewed on Aug. 3, 2025

Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

5 out of 5
Fells Point
per person
Sep 20 - Sep 23
found 9 hours ago
Roundtrip non-stop flight included
Regina (YQR) to Baltimore (BWI)
9.4/10 Exceptional! (1,000 reviews)
Beautiful, professional establishment.

Reviewed on Aug. 3, 2025

Ready to book your vacation to Chesapeake City?

 

Choose your dates

Chesapeake City Hotel Deals

Historic Chesapeake City Stay

Historic Chesapeake City Stay

Chesapeake City
The price is CA $149 per night from Aug 5 to Aug 6
CA $149
CA $384 total
Aug 5 - Aug 6
includes taxes & fees
9.2/10 Wonderful! (9 reviews)
Perfect
"Perfect little place for 2. Quiet Very close to Schaefers."

Reviewed on Jul. 7, 2025

Historic Chesapeake City Stay
Sonesta Select Newark Christiana Mall

Sonesta Select Newark Christiana Mall

3 out of 5
48 Geoffrey Dr, Newark, DE
Fully refundableReserve now, pay when you stay
The price is CA $133 per night from Aug 5 to Aug 6
CA $133
CA $148 total
Aug 5 - Aug 6
includes taxes & fees
7.8/10 Good! (1,046 reviews)
"Lobby and room were nice. Everything in between not so much - carpet was in poor shape, seemed run down. Staff was good, didn't interact with them a lot."

Reviewed on Aug. 1, 2025

Sonesta Select Newark Christiana Mall
Extended Stay America Suites Newark Christiana Wilmington

Extended Stay America Suites Newark Christiana Wilmington

2.5 out of 5
333 Continental Dr, Newark, DE
Fully refundableReserve now, pay when you stay
The price is CA $105 per night from Aug 10 to Aug 11
CA $105
CA $117 total
Aug 10 - Aug 11
includes taxes & fees
6/10 (1,000 reviews)
"Alicia at the front desk was awesome! She was very busy and she remained friendly and professional. My room was clean and inviting. I thoroughly enjoyed my stay and would be happy to stay here again if I’m traveling in the area."

Reviewed on Jul. 22, 2025

Extended Stay America Suites Newark Christiana Wilmington
See all 573 properties in Chesapeake City
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Chesapeake City

C and D Canal Museum

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.

C and D Canal Museum

Frequently asked questions

How much does a Chesapeake City vacation package cost?
You can grab a vacation package to this popular destination from CA $637 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.