Chesapeake Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Plan, 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.

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Chesapeake Hotel Deals

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 CA $122 per night from Aug 2 to Aug 3
CA $122
CA $138 total
Aug 2 - Aug 3
includes taxes & fees
8/10 Very good! (1,000 reviews)
"Everything was pretty good, breakfast was solid and decently fresh"

Reviewed on Jul 8, 2026

Charleston Marriott Town Center
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 CA $172 per night from Jul 26 to Jul 27
CA $172
CA $194 total
Jul 26 - Jul 27
includes taxes & fees
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 CA $119 per night from Aug 2 to Aug 3
CA $119
CA $135 total
Aug 2 - Aug 3
includes taxes & fees
8.6/10 Excellent! (1,166 reviews)
"Clean, comfortable. Breakfast was good, above average, and the coffee was the best I have had in any hotel."

Reviewed on Jul 13, 2026

Holiday Inn Express Charleston-Civic Center by IHG
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.

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.