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
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Your Chesapeake Vacation
Say bye-bye to planning worries and hello to a Chesapeake vacation package. With everything organized before you leave, you can focus on discovering every inch of this city, starting with Burlington, which is good for history, dining and shopping. You'll want to sightsee during your trip to Chesapeake. Make time for big-name attractions such as Huntington Museum of Art, Keith Albee Theatre and Mountain Health Arena. Don't delay your visit to this city any longer. Your perfect Chesapeake vacation is a few quick clicks away with Expedia.
Top Chesapeake Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Comfort Inn Barboursville near Huntington Mall area
CA $1,340
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Huntington (HTS)
8.2/10 Very good! (839 reviews)
Staff had informed me one thing at the phone and informed Expedia something different, I was charged for a night I haven’t stayed and when we finally arrived there the bedroom was awful, besides the dirty bed sheets there was a ton of stinky bugs, the only reason I’m nor giving zero stars is because there was one girl at the front desk that was nice
Reviewed on Oct 12, 2026
Ready to book your vacation to Chesapeake?
Chesapeake Hotel Deals
DoubleTree by Hilton Huntington
1001 3rd Avenue Huntington WV
Fully refundableReserve now, pay when you stay
CA $156
CA $177 total
Nov 1 - Nov 2
includes taxes & fees
Delta Hotels by Marriott Huntington Downtown
800 3rd Ave Huntington WV
CA $184
CA $208 total
Oct 18 - Oct 19
includes taxes & fees
Rodeway Inn
3441 US Route 60 E Barboursville WV
Fully refundable
CA $101
CA $114 total
Oct 19 - Oct 20
includes taxes & fees
7.2/10 Good! (1,004 reviews)
"Price"
Reviewed on Oct 12, 2026
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 from CA $1,279 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 many days is enough for Chesapeake?
With about 2 days, you'll have plenty of time to experience popular neighbourhoods like Brentwood and Burlington during your Chesapeake vacation. Remember to also add Pullman Square and Huntington Museum of Art to your sightseeing itinerary. In the mood for more adventures? Consider exploring outside of Chesapeake on day trips and tours.
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," "Traveller 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 travellers 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
