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.
DoubleTree by Hilton Hotel Laurel

DoubleTree by Hilton Hotel Laurel

4 out of 5
West Laurel
Price was CA $901, price is now CA $585 per person
CA $585
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Baltimore (BWI)
8.2/10 Very Good! (1,006 reviews)
Convenient external room door made it easy walking my dog. Did not have to walk thru.obby.

Reviewed on Aug. 24, 2025

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
Price was CA $1,610, price is now CA $1,188 per person
CA $1,188
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Baltimore (BWI)
8.6/10 Excellent! (1,008 reviews)
Night staff at desk not so nice

Reviewed on Aug. 24, 2025

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
Price was CA $1,879, price is now CA $1,413 per person
CA $1,413
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Baltimore (BWI)
9.4/10 Exceptional! (1,008 reviews)
Great location and fun hotel theme! Very nice staff. Walked to shops and food - loved Boatyard Restaurant. Thank you!

Reviewed on Aug. 20, 2025

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
Historic District
Price was CA $1,338, price is now CA $1,022 per person
CA $1,022
per person
Nov 7 - Nov 9
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
9/10 Wonderful! (1,831 reviews)
Fire alarm went off at 1am and had to evacuate, no explanation, fire dept told us we could return. Room was several blocks from checkin location- would have been nice to know ahead of time so we wouldn’t have lugged our luggage across town.

Reviewed on Aug. 24, 2025

Hotel Ulysses, a Member of Design Hotels

Hotel Ulysses, a Member of Design Hotels

4 out of 5
Mount Vernon
Price was CA $1,005, price is now CA $770 per person
CA $770
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Baltimore (BWI)
9.2/10 Wonderful! (925 reviews)
Staff was super friendly and communicative. They were accommodating and the vibe of this place is immaculate. Maximalist and beautiful. Every detail is taken care of.

Reviewed on Aug. 24, 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 28 to Aug 29
CA $149
CA $385 total
Aug 28 - Aug 29
includes taxes & fees
8.8/10 Excellent! (12 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 26 to Aug 27
CA $133
CA $148 total
Aug 26 - Aug 27
includes taxes & fees
7.8/10 Good! (1,082 reviews)
"I’ve stayed here multiple times in this last time was probably the best. The staff was very helpful and courteous, and the amenities were top-notch."

Reviewed on Aug. 18, 2025

Sonesta Select Newark Christiana Mall
Quality Inn Newark - Wilmington

Quality Inn Newark - Wilmington

2.5 out of 5
65 Geoffrey Dr, Newark, DE
Fully refundableReserve now, pay when you stay
The price is CA $87 per night from Aug 26 to Aug 27
CA $87
CA $97 total
Aug 26 - Aug 27
includes taxes & fees
5/10 (1,002 reviews)
"There is a door that is tetanus waiting to happen its rusy and my friend cut her hand trying to get to the second floor. But the staff is amazing . The man who checked us in was great. The room was clean however they should get new beds in 242 they are loud and a little uncomfy but for a night or ..."

Reviewed on Aug. 21, 2025

Quality Inn Newark - Wilmington
See all 575 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.
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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 $585 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.