Chesapeake Holidays

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    Save up to S$1,300 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Top hotels in Chesapeake

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 S$130 per night from 2 Aug to 3 Aug
S$130
2 Aug - 3 Aug
includes taxes & fees
8.6/10 Excellent! (1,160 reviews)
"First impressions are lasting, and last impressions are the first thing people remember. When I first arrived, I needed to use a restroom. The staff directed me to the men's bathroom. I used it, and there was no soap, hand sanitizer, or hand towels. There was an automatic hand dryer. Because I was ..."

Reviewed on 8 Jul, 2026

Holiday Inn Express Charleston-Civic Center by IHG
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 S$187 per night from 12 Jul to 13 Jul
S$187
12 Jul - 13 Jul
includes taxes & fees
8.4/10 Very good! (1,435 reviews)
"Nice clean place great breakfast"

Reviewed on 9 Jul, 2026

Embassy Suites Charleston
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 S$139 per night from 20 Jul to 21 Jul
S$139
20 Jul - 21 Jul
includes taxes & fees
8/10 Very good! (1,009 reviews)
"Everything was pretty good, breakfast was solid and decently fresh"

Reviewed on 8 Jul, 2026

Charleston Marriott Town Center
See all 158 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.

What to do in Chesapeake

Astonishing Scavenger Hunt: West Virginia’s Cultural Crown!

Astonishing Scavenger Hunt: West Virginia’s Cultural Crown!

S$16
per adult
Astonishing Scavenger Hunt: West Virginia’s Cultural Crown!
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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.