Chesapeake Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
Your Chesapeake Vacation
Food, history, entertainment and more … There's so much to discover with a Chesapeake vacation package. And with the ability to customize your city break, it's guaranteed to be one that's tough to forget. Cabin Creek Quilts is one of the famous attractions to put on your to-do list during a trip to Chesapeake. Your ultimate Chesapeake vacation is a couple of clicks away. Browse flights, accommodations and more on Expedia for an adventure that's tailored to suit your travel style.
Ready to book your vacation to Chesapeake?
Chesapeake Hotel Deals
Charleston Marriott Town Center
200 Lee St E Charleston WV
Fully refundableReserve now, pay when you stay
CA $110
CA $124 total
Sep 13 - Sep 14
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 Aug 30, 2026
Embassy Suites Charleston
300 Court St Charleston WV
Fully refundableReserve now, pay when you stay
CA $158
CA $179 total
Sep 7 - Sep 8
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 Aug 31, 2026
Holiday Inn Express Charleston-Civic Center by IHG
100 Civic Center Drive Charleston WV
Fully refundable
CA $140
CA $159 total
Sep 13 - Sep 14
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.
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! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Chesapeake?
If you'd like to score a cheap Chesapeake vacation package, consider visiting in January, February and November. You're likely to find lower rates on hotels and airfares during these quieter months — perfect for travellers wishing to save money.
How many days is enough for Chesapeake?
The ideal duration for your Chesapeake vacation depends on what you'd like to do. Generally, a handful of days to a week will give you enough time to go to all the top sights and discover some hidden spots along the way.
How to find the best Chesapeake package deals?
Start your search for a Chesapeake package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Chesapeake package deal straight away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Chesapeake getaway off to a flying start.
Is it cheaper to book a Chesapeake vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll generally get a better deal than booking each component separately. And you'll still have the flexibility to create a tailored Chesapeake vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Chesapeake?
If you have your Chesapeake vacation dates finalized, book as early as you can to grab some awesome deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Chesapeake?
- Pick the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to travel to Chesapeake.
- Set a budget: Factor in costs such as flights, food and transportation when calculating how much to save for your trip to Chesapeake. Then, choose a hotel that matches your budget, whether that's an economical option or a high-end getaway.
- Decide how long to go away for: Now that you know more about Chesapeake, you can figure out the right length of your break. Create a rough plan and give yourself enough time to cover everything you want to do.
- Combine your flights and hotel: Epic 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.
