Chesapeake Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Top hotels in Chesapeake

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$188 per night from 3 Aug to 4 Aug
S$188
3 Aug - 4 Aug
includes taxes & fees
8.4/10 Very Good! (1,209 reviews)
"Loved the size of the room. The only issue I had was with lighting. Not much light in the bathroom so hard to put on makeup."

Reviewed on 12 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 S$126 per night from 20 Jul to 21 Jul
S$126
20 Jul - 21 Jul
includes taxes & fees
8.6/10 Excellent! (1,083 reviews)
"Quiet area, kind staff, surprisingly good hot breakfast."

Reviewed on 10 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 S$159 per night from 21 Jul to 22 Jul
S$159
21 Jul - 22 Jul
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
"Went to the hotel to stay for a Heart Concert. Although the hotel was crowded the staff was very efficient and helpful. Liked that is was right across the street from the show."

Reviewed on 11 Jul, 2025

Charleston Marriott Town Center
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

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. 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.