Chesapeake Vacations

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  • Plan, book, travel with confidence

  • Better together

    Save up to AEDĀ 5,000 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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    Plan, book, and manage your trip all in one place

Find the Best Chesapeake Vacation Packages

Chesapeake Hotel Deals

DoubleTree by Hilton Huntington

DoubleTree by Hilton Huntington

4 out of 5
1001 3rd Avenue Huntington WV
Fully refundableReserve now, pay when you stay
The price is AEDĀ 389 per night from Aug 16 to Aug 17
AEDĀ 389
AEDĀ 439 total
16 Aug - 17 Aug
includes taxes & fees
DoubleTree by Hilton Huntington
Fairfield Inn & Suites by Marriott Huntington

Fairfield Inn & Suites by Marriott Huntington

3 out of 5
536 Kinetic Drive Huntington WV
Fully refundableReserve now, pay when you stay
The price is AEDĀ 418 per night from Aug 9 to Aug 10
AEDĀ 418
AEDĀ 473 total
9 Aug - 10 Aug
includes taxes & fees
Fairfield Inn & Suites by Marriott Huntington
Delta Hotels by Marriott Huntington Downtown

Delta Hotels by Marriott Huntington Downtown

3 out of 5
800 3rd Ave Huntington WV
Fully refundableReserve now, pay when you stay
The price is AEDĀ 511 per night from Jul 26 to Jul 27
AEDĀ 511
AEDĀ 577 total
26 Jul - 27 Jul
includes taxes & fees
Delta Hotels by Marriott Huntington Downtown
See all 197 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.

Frequently asked questions

How much does a Chesapeake vacation package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a vacation to Chesapeake costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Chesapeake?
To pick up cheap Chesapeake vacation packages, plan your getaway outside of peak times such as public holidays. You'll typically find better availability and lower prices when it's less busy.
How to find the best Chesapeake package deals?
Landing a cheap Chesapeake package deal is a cinch with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget, add some filters and see what's available. You can personalize your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to view the most wallet-friendly Chesapeake package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Chesapeake vacation as a package?
You can enjoy significant savings on your next Chesapeake break by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to view the best hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Chesapeake?
If you've got your Chesapeake vacation dates confirmed, book as soon as you can to grab some terrific deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Chesapeake?

  1. Choose when to travel: Check your schedule and get your bags packed. Your preferred season and the activities available will also help you decide when to visit Chesapeake.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and meals to flights and activities. Your hotel will probably be the biggest expense during your trip to Chesapeake.
  3. Work out your trip length: Consider how much time you want to spend discovering Chesapeake. Plan your days so you can get to all the activities and attractions you're interested in at a leisurely pace.
  4. Bundle your flights and hotel: 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.