Chesapeake City Holidays from NZ$2,725

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The Latest Chesapeake City Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

2.5 out of 5
per person
27 Sept - 29 Sept
found 1 day ago
Return direct flight included
Auckland (AKL) to Baltimore (BWI)
8.2/10 Very Good! (1,005 reviews)
We encountered issues at check-in in but they could fix it relatively fast. The water did not get that hot, the carpet was dirty and the room was very dark even with all of the lights on. But the staff was excellent!

Reviewed on 11 Aug. 2025

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
per person
27 Sept - 29 Sept
found 1 day ago
Return direct flight included
Auckland (AKL) to Baltimore (BWI)
9.4/10 Exceptional! (1,002 reviews)
Beautiful hotel in a great location!

Reviewed on 10 Aug. 2025

Sandaway Suites & Beach

Sandaway Suites & Beach

3 out of 5
per person
27 Sept - 29 Sept
found 1 day ago
Return direct flight included
Auckland (AKL) to Baltimore (BWI)
9.4/10 Exceptional! (144 reviews)
Beautiful historic building and rooms. Scenic, quiet grounds, calming views of the bay. A true gem !

Reviewed on 3 Aug. 2025

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
Historic District
per person
27 Sept - 29 Sept
found 1 day ago
Return direct flight included
Auckland (AKL) to Baltimore (BWI)
9/10 Wonderful! (1,824 reviews)
Charming area and loved to hotel decor!

Reviewed on 11 Aug. 2025

134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel

2.5 out of 5
per person
27 Sept - 29 Sept
found 1 day ago
Return direct flight included
Auckland (AKL) to Baltimore (BWI)
9.6/10 Exceptional! (20 reviews)
Fantastic hotel with exceptional service and attention to detail. Debbie and the other members of staff were warm and welcoming, nothing was to much trouble. Look forward to staying there again in the future. Thank you for a wonderful stay.

Reviewed on 22 Jan. 2023

Chesapeake City Holiday

Our pick of the best Chesapeake City Hotel Deals

Historic Chesapeake City Stay

Historic Chesapeake City Stay

Chesapeake City
The price is NZ$468 per night from 13 Aug to 14 Aug
NZ$468
13 Aug - 14 Aug
includes taxes & fees
9/10 Wonderful! (11 reviews)
Perfect
"Perfect little place for 2. Quiet Very close to Schaefers."

Reviewed on 7 Jul. 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 NZ$189 per night from 25 Aug to 26 Aug
NZ$189
25 Aug - 26 Aug
includes taxes & fees
7.8/10 Good! (1,058 reviews)
"Overall comfort"

Reviewed on 6 Aug. 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 NZ$145 per night from 17 Aug to 18 Aug
NZ$145
17 Aug - 18 Aug
includes taxes & fees
6/10 (1,002 reviews)
"Perfect place for me. I will be extending my stay at least another week/month. Great kitchen! Yeah! Patrick Dougherty. Room 232!👍"

Reviewed on 3 Aug. 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.

Discover the most popular places to visit in Chesapeake City

Bohemia Vista Marina

Explore the waterfront in Chesapeake City with a trip to Bohemia Vista Marina. While in this family-friendly area, you can savour the top-notch restaurants.

Bohemia Vista Marina

C and D Canal Museum

You can spend time exploring the galleries in C and D Canal Museum during your travels in Chesapeake City. While you're here, you can savour the top-notch restaurants.

C and D Canal Museum

Frequently asked questions

How much does a Chesapeake City holiday package cost?
You'll find cheap prices from NZ$2,725 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 holiday to Chesapeake City costs.
What are the cheapest months to go to Chesapeake City?
If you're looking to snag a cheap Chesapeake City holiday package, consider travelling 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 holiday 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 holiday package as soon as possible.
Is it cheaper to book a Chesapeake City holiday as a package?
An Expedia holiday 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 holiday package to Chesapeake City?
If you've got your Chesapeake City holiday 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, favourite 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 accommodation, 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 accommodation and airfare: After you've nailed down your dates and duration, lock in the ideal Chesapeake City holiday package for you.

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