Chesapeake City Vacations from $160

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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.
Beacon Hotel & Corporate Quarters

Beacon Hotel & Corporate Quarters

3.5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $244, price is now $160 per person
$160
per person
Aug 28 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
7.6/10 Good! (1,019 reviews)

Hotel Burg

Hotel Burg

4 out of 5
Leesburg's Old and Historic District
Save 100% on your flight
Price was $1,674, price is now $1,005 per person
$1,005
per person
Oct 2 - Oct 5
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
9.6/10 Exceptional! (94 reviews)

The River Inn

The River Inn

4 out of 5
Northwest
Save 100% on your flight
Price was $1,141, price is now $712 per person
$712
per person
Oct 4 - Oct 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (2,011 reviews)
Incredible stay at The River Inn. The front desk staff was lovely and so helpful when we needed anything. We will be back.

Reviewed on Jul 19, 2026

Phoenix Park Hotel

Phoenix Park Hotel

3.5 out of 5
Northwest
Save 100% on your flight
Price was $1,164, price is now $730 per person
$730
per person
Oct 4 - Oct 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (2,206 reviews)
Good

Reviewed on Jul 18, 2026

Hotel Washington

Hotel Washington

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $1,635, price is now $1,038 per person
$1,038
per person
Oct 4 - Oct 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (2,426 reviews)
Location, location, location. The hotel and staff were 10 Star. The room service and food choices were excellent. The rooftop bar and the view provided are not to be missed.

Reviewed on Jul 19, 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.
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Chesapeake City Hotel Deals

HYDRANGEA HOUSE Waterview cozy 3-bdrm Getaway in quiet Chesapeake City AC & yard

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

Get rates
HYDRANGEA HOUSE Waterview cozy 3-bdrm Getaway in quiet Chesapeake City AC & yard
Quality Inn Newark - Wilmington

Quality Inn Newark - Wilmington

2.5 out of 5
65 Geoffrey Dr Newark DE
Fully refundable
$65 nightly
The price is $72 total per night from Jul 26 to Jul 27
$72 total
Jul 26 - Jul 27
Total with taxes and fees
Quality Inn Newark - Wilmington
Great Wolf Lodge Perryville

Great Wolf Lodge Perryville

2 out of 5
1240 Chesapeke Overlook Parkway Perryville MD
$199 nightly
The price is $223 total per night from Jul 28 to Jul 29
$223 total
Jul 28 - Jul 29
Total with taxes and fees
Great Wolf Lodge Perryville
See all 595 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 $160 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.