Chesapeake City Vacations from ￥274,168

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The Latest Chesapeake City Vacation Packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Baltimore North - Pikesville

DoubleTree by Hilton Baltimore North - Pikesville

4 out of 5
Price was ￥280,900, price is now ￥274,168 per person
￥274,168
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Baltimore (BWI)
8/10 Very Good! (1,000 reviews)
The poperty was in a great place for traveling. The room was clean and staff were professional. My disappointment was in the room. I guess at some point the air system and they put the floor model air conditioners in the room that vent through the window. That is not an issue with me, is it how it was vent. Just little pieces of duct tape holding it to the window which still allowed the access heat in the room that we had on the 4th floor.

Reviewed on Jul 6, 2026

Pendry Baltimore

Pendry Baltimore

5 out of 5
Fells Point
Price was ￥436,516, price is now ￥402,137 per person
￥402,137
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Baltimore (BWI)
9.4/10 Exceptional! (1,003 reviews)
I purchased my stay with Expedia and ThebPendry charged my credit card again for a room I already paid for. I called twice and situation was never resolved. I have no problem paying for my stay but, I do not like anyone stealing from me. Horrendous!

Reviewed on Jul 6, 2026

The William Fell Baltimore, Tapestry Collection by Hilton

The William Fell Baltimore, Tapestry Collection by Hilton

3.5 out of 5
Fells Point
Price was ￥378,382, price is now ￥363,546 per person
￥363,546
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Baltimore (BWI)
9.2/10 Wonderful! (218 reviews)
Clean room, great service!

Reviewed on Jul 6, 2026

The Hotel at Arundel Preserve

The Hotel at Arundel Preserve

3.5 out of 5
Arundel Mills
Price was ￥294,904, price is now ￥285,003 per person
￥285,003
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Baltimore (BWI)
9.4/10 Exceptional! (1,848 reviews)
This hotel was super clean and the staff was amazing

Reviewed on Jul 6, 2026

Sheraton Baltimore Washington Airport Hotel - BWI

Sheraton Baltimore Washington Airport Hotel - BWI

3.5 out of 5
Price was ￥283,502, price is now ￥276,666 per person
￥276,666
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Baltimore (BWI)
8.2/10 Very Good! (384 reviews)
Comfortable beds. Helpful staff.

Reviewed on Jul 5, 2026

Find the Best Chesapeake City Vacation Packages

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
The price is ￥9,969 per night from Jul 21 to Jul 22
￥9,969
￥11,065 total
Jul 21 - Jul 22
includes taxes & fees
5.8/10 (1,010 reviews)
"Nothing was wrong with anything"

Reviewed on Jul 6, 2026

Quality Inn Newark - Wilmington
Great Wolf Lodge Perryville

Great Wolf Lodge Perryville

2 out of 5
1240 Chesapeke Overlook Parkway Perryville MD
The price is ￥29,007 per night from Jul 20 to Jul 21
￥29,007
￥32,487 total
Jul 20 - Jul 21
includes taxes & fees
8.8/10 Excellent! (251 reviews)
"Y"

Reviewed on Jul 5, 2026

Great Wolf Lodge Perryville
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.

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

Frequently asked questions

How much does a Chesapeake City vacation package cost?
You'll find cheap prices from ￥274,168 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?
If you're looking to snag a cheap Chesapeake City vacation package, consider traveling in April, June and October. You'll typically find lower prices on airfares and hotels during these quieter months — perfect for a budget-friendly break.
How many days is enough for Chesapeake City?
The ideal length for your Chesapeake City vacation depends on what you'd like to see. Usually, a handful of days to a week will give you enough time to check out all the major sights and discover some hidden gems 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.
How to plan a trip to Chesapeake City?

  1. Choose the ideal time to travel: Your schedule, favorite season and the type of weather you enjoy can all influence your decision on when to go to Chesapeake City.
  2. Plan your budget wisely: In addition to the cost of your accommodations, you should factor in other expenses too. These include transportation, food and flights. Also, set aside a little extra for unexpected costs that may come up during your trip to Chesapeake City.
  3. Work out your trip length: Consider how long you want to spend exploring Chesapeake City. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Combine your accommodations and airfare: After you've nailed down your dates and duration, lock in the ideal Chesapeake City vacation package for you.

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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.