Chesapeake Holidays

Book a Hotel + Flight or Car together to unlock savings

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    Find the right fit

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Your Chesapeake Holiday

With a Chesapeake holiday package, say goodbye to endless planning and hello to an effortless adventure. Every detail of your journey has been taken care of before you go, so you can make the most of your time discovering this exciting city. Like some inspiration on what to see or do first during your trip to Chesapeake? Head straight for top attractions such as Cabin Creek Quilts. No matter your travel plans or budget, putting together a tailored Chesapeake holiday is easy with Expedia.

Chesapeake Holiday

Chesapeake Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Yeager Airport (CRW)
Population
1,500
Max Temp Winter
7ºC
Max Temp Summer
29ºC
Top Sights
West Virginia State Museum, Kanawha State Forest and Children s Theatre of Charleston

Our pick of the best Chesapeake Hotel Deals

Embassy Suites Charleston
Embassy Suites Charleston
3.5 out of 5
300 Court St, Charleston, WV
Fully refundableReserve now, pay when you stay
The price is AU$224 per night from 20 July to 21 July
AU$224
20 July - 21 July
includes taxes & fees
8.4/10 Very Good! (1,198 reviews)
"Great stay!"

Reviewed on 7 Jul. 2025

Embassy Suites Charleston
Holiday Inn Express Charleston-Civic Center by IHG
Holiday Inn Express Charleston-Civic Center by IHG
2.5 out of 5
100 Civic Center Drive, Charleston, WV
Fully refundable
The price is AU$151 per night from 13 July to 14 July
AU$151
13 July - 14 July
includes taxes & fees
8.6/10 Excellent! (1,081 reviews)
"All good"

Reviewed on 6 Jul. 2025

Holiday Inn Express Charleston-Civic Center by IHG
Charleston Marriott Town Center
Charleston Marriott Town Center
3.5 out of 5
200 Lee St E, Charleston, WV
Fully refundableReserve now, pay when you stay
The price is AU$190 per night from 20 July to 21 July
AU$190
20 July - 21 July
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
"Very comfortable"

Reviewed on 29 Jun. 2025

Charleston Marriott Town Center
See all 169 properties in Chesapeake
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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

What to do in Chesapeake

Charleston Let’s Roam Treasure Hunt:West Virginia’s Cultural Crown!

Self-Guided Scavenger Hunt: West Virginia’s Cultural Crown!

AU$20
per adult
Self-Guided Scavenger Hunt: West Virginia’s Cultural Crown!
Promise Land Bee Farm Private Tour in Charleston

Promise Land Bee Farm Private Tour in Charleston

AU$78
per adult
Promise Land Bee Farm Private Tour in Charleston
See all activities in Chesapeake

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?

  1. Choose your dates: The things you'd like to do in Chesapeake and your preferred season can help you decide when to get away.
  2. 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.
  3. 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.
  4. 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.