Chesapeake Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Chesapeake Holiday
Our pick of the best Chesapeake Hotel Deals
Charleston Marriott Town Center
200 Lee St E Charleston WV
Fully refundableReserve now, pay when you stay
NZ$151
13 Sept - 14 Sept
includes taxes & fees
8/10 Very good! (1,005 reviews)
"It was an ok stay. Parking is confusing, you end up paying $15 just to find a closer parking lot for free because it was an exit only where you get in from the street. Rooms were not super clean. Bathroom had random hairs every where, bed sheets stained. Walls disgusting. Breakfast is expensive for ..."
Reviewed on 30 Aug 2026
Embassy Suites Charleston
300 Court St Charleston WV
Fully refundableReserve now, pay when you stay
NZ$218
7 Sept - 8 Sept
includes taxes & fees
8.4/10 Very good! (1,457 reviews)
"The only real issue was with the elevators. They have 3 elevators and only one was working, which made for a very long wait coming and going. We heard the elevators have not worked for a while so that is an issue. That 3rd elevator is bound to go down also."
Reviewed on 31 Aug 2026
Holiday Inn Express Charleston-Civic Center by IHG
100 Civic Center Drive Charleston WV
Fully refundable
NZ$193
13 Sept - 14 Sept
includes taxes & fees
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.
What to do in Chesapeake
Astonishing Scavenger Hunt: West Virginia’s Cultural Crown!
NZ$21
per adult
Frequently asked questions
How much does a Chesapeake holiday package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Chesapeake costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Chesapeake?
If you'd like to score a cheap Chesapeake holiday package, consider planning a trip in January, February and November. You'll usually find lower rates on hotels and airfares during these months — ideal for travellers wishing to save money.
How many days is enough for Chesapeake?
Generally, a handful of days is enough to explore the main attractions during your Chesapeake holiday. However, if you prefer to have more time to chill out or go on day tours, consider extending your trip.
How to find the best Chesapeake package deals?
Use Expedia's handy filters to find some unbeatable Chesapeake package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Chesapeake package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your holiday package as soon as possible.
Is it cheaper to book a Chesapeake holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically land a better deal than booking each component separately. And you'll still have the freedom to create a customised Chesapeake holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday package to Chesapeake?
If you have your Chesapeake travel dates locked in, book early to grab some incredible deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Chesapeake?
- Choose your dates: The things you'd like to do in Chesapeake and your preferred season can help you decide when to get away.
- Calculate your budget: Ensure you have enough money to cover everything from transportation and meals to experiences and flights. Your hotel will probably be the biggest expense during your trip to Chesapeake.
- Decide how many days away: Start by listing all the sights and activities you'd like to get to in Chesapeake. Then, estimate how long you'll need for each, including any travel time.
- Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to choose a Chesapeake holiday 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.
