Chesapeake Trips (flight + hotel)

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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 P7,315 per night from Jul 13 to Jul 14
P7,315
P8,265 total
Jul 13 - Jul 14
includes taxes & fees
8.4/10 Very Good! (1,186 reviews)
"We went the the Charleston Regatta. This hotel was walking distance. The valet parking was great! Great breakfast also."

Reviewed on Jul 5, 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 P7,934 per night from Aug 4 to Aug 5
P7,934
P8,965 total
Aug 4 - Aug 5
includes taxes & fees
8.6/10 Excellent! (1,084 reviews)
"Rooms were a little dated and there was hair everywhere. On the bright side breakfast was really really good. You could tell the preparers really cared vs. just warming things up. I took pictures of the hair on the floor and underneath the sink, but of course I deleted them."

Reviewed on Jul 2, 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 P6,207 per night from Jul 13 to Jul 14
P6,207
P7,014 total
Jul 13 - Jul 14
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Very comfortable"

Reviewed on Jun 29, 2025

Charleston Marriott Town Center
See all 168 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.

Popular places to visit

West Virginia State Capitol Building featuring heritage architecture and an administrative buidling

West Virginia State Capitol Building

Take a guided tour around West Virginia’s seat of government and marvel at its dazzling dome, which is covered in 23.5-karat gold.

West Virginia State Capitol Building

Laidley Field

Explore the great outdoors at Laidley Field, a lovely green space in Charleston. While in this walkable area, find time to visit its casinos.

Laidley Field

CAMC Memorial Hospital

Though CAMC Memorial Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Charleston while you are here.

CAMC Memorial Hospital

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!

P719
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

P2,809
per adult
Promise Land Bee Farm Private Tour in Charleston
See all activities in Chesapeake

Frequently asked questions

How much does a Chesapeake vacation package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a vacation 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 vacation 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 travelers 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 vacation. 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 vacation package as soon as possible.
Is it cheaper to book a Chesapeake vacation as a package?
Expedia vacation 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 customized Chesapeake vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation 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 vacation 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.