Chesapeake Vacations
Book a Hotel + Flight together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to SAR 5,400 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
Find the Best Chesapeake Vacation Packages
Chesapeake Hotel Deals
DoubleTree by Hilton Huntington
1001 3rd Avenue Huntington WV
Fully refundableReserve now, pay when you stay
SAR 428
SAR 484 total
13 Sep - 14 Sep
includes taxes & fees
8.4/10 Very Good! (1,011 reviews)
"I would not rate this hotel 4 star . It was not well kept up. The walls were scuffed up, the carpeting was old, the chair in our room was so sunk in, you couldn't even sit in it. I would not stay there again."
Reviewed on 31 August 2026
Delta Hotels by Marriott Huntington Downtown
800 3rd Ave Huntington WV
Fully refundableReserve now, pay when you stay
SAR 484
SAR 547 total
6 Sep - 7 Sep
includes taxes & fees
Fairfield Inn & Suites By Marriott Ashland
10945 Route 60 Ashland KY
Fully refundableReserve now, pay when you stay
SAR 385
SAR 437 total
6 Sep - 7 Sep
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 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?
- 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.
- 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.
- 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.
- 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.
