Chesapeake City Vacations from $251

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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.

The Latest Chesapeake City vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Hive

Hotel Hive

3.5 out of 5
Northwest
Save 100% on your flight
Price was $382, price is now $251 per person
$251
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.2/10 Wonderful! (1,509 reviews)
Quick trip to DC, and Hotel Hive was the perfect place to start the day! Great location, cool vibe, fun roof top bar and great staff. We will definitely return!

Reviewed on Jul 4, 2026

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $1,059, price is now $570 per person
$570
per person
Sep 24 - Sep 30
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.8/10 Excellent! (1,001 reviews)
The air-conditioning was very loud. There is no central airflow. The indoor unit is very loud, it is very difficult to sleep next to it. Also we were on the top floor near the elevator, it was very noisy, there was constant noise.

Reviewed on Jun 28, 2026

Salamander Washington DC

Salamander Washington DC

5 out of 5
Southwest
Save 100% on your flight
Price was $1,131, price is now $692 per person
$692
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (1,106 reviews)
My stay was everything I could have imagined. The staff were extremely friendly and attentive. Hospitality was 10 out of 10. The spa services were amazing. Would definitely stay here again.

Reviewed on Jul 2, 2026

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
Historic District
Save 100% on your flight
Price was $786, price is now $518 per person
$518
per person
Aug 12 - Aug 18
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
9/10 Wonderful! (1,866 reviews)
The room was very dark. No outside window in our room.

Reviewed on Jul 4, 2026

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
Price was $401, price is now $270 per person
$270
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,005 reviews)
Awesome staff and such a variety of food! Place is so convenient!

Reviewed on Jul 4, 2026

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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.
See properties

Chesapeake City Hotel Deals

Quality Inn Newark - Wilmington

Quality Inn Newark - Wilmington

2.5 out of 5
65 Geoffrey Dr Newark DE
Fully refundable
$60 nightly
The price is $67 total per night from Jul 20 to Jul 21
$67 total
Jul 20 - Jul 21
Total with taxes and fees
5.8/10 (1,005 reviews)
"The general area was not well maintained or clean. The room was not that clean and the bathtub had paint chips and looked stained. The pool area had trash all over it. The location was great. It is not a good Quality Inn."

Reviewed on Jul 4, 2026

Quality Inn Newark - Wilmington
Great Wolf Lodge Perryville

Great Wolf Lodge Perryville

2 out of 5
1240 Chesapeke Overlook Parkway Perryville MD
$179 nightly
The price is $200 total per night from Jul 20 to Jul 21
$200 total
Jul 20 - Jul 21
Total with taxes and fees
8.8/10 Excellent! (249 reviews)
"Decent indoor pool and slides available at a decent rate. I wouldn’t pay more than 250 a night to stay here which includes the day passes to the water park but for 250 a day or less, it’s worth the trip."

Reviewed on Jul 2, 2026

Great Wolf Lodge Perryville
Red Roof Inn & Suites Newark - University

Red Roof Inn & Suites Newark - University

2 out of 5
1119 S College Avenue Newark DE
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $85 total per night from Jul 6 to Jul 7
$85 total
Jul 6 - Jul 7
Total with taxes and fees
5.6/10 (1,000 reviews)
"Yes"

Reviewed on Jun 29, 2026

Red Roof Inn & Suites Newark - University
See all 583 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.

Find the Best Chesapeake City Vacation Packages

Chesapeake City Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Wilmington, DE (ILG-New Castle)
Population
690
Max Temp Winter
40ºF
Max Temp Summer
85ºF
Top Sights
Elk Neck State Park, Historical Society of Cecil County and Milburn Stone Theater

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Frequently asked questions

How much does a Chesapeake City vacation package cost?
You'll find cheap prices from $251 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 vacation to Chesapeake City costs.
What are the cheapest months to go to Chesapeake City?
November, December and January are great times to look for cheap Chesapeake City vacation packages. Traveling in less busy months means you'll typically find lower prices on accommodations and flights.
How many days is enough for Chesapeake City?
The ideal length for your Chesapeake City vacation depends on what you'd like to do. Usually, a handful of days to a week will give you enough time to go to all the leading sights and explore some hidden treasures 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 vacation package as soon as possible.
Is it cheaper to book a Chesapeake City vacation as a package?
An Expedia vacation 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 vacation package to Chesapeake City?
If you've got your Chesapeake City vacation 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.
Does Expedia offer Book Now, Pay Later Chesapeake City vacation packages?
Secure your dream escape to Chesapeake City with help from our Book Now, Pay Later vacations. No need to save like crazy or hold off until payday — we've partnered with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans mean you can split the cost over 3, 6 or 12 months. With no late payment fees or extra charges, you can easily stay on budget and snap up travel deals before they disappear.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.