Chesapeake Vacation Packages

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

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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.

Ready to book your vacation to Chesapeake?

 

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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 CA $150 per night from Aug 2 to Aug 3
CA $150
CA $169 total
Aug 2 - Aug 3
includes taxes & fees
8.4/10 Very good! (1,013 reviews)
"We basically just slept here but we had a fantastic weekend and the staff here was amazing!! The beds and pillows were super comfy!"

Reviewed on Jul 12, 2026

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 CA $171 per night from Jul 26 to Jul 27
CA $171
CA $193 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
"$750 for two nights and no maid service the first day??? Some excuse about Covid was given....give me a break!!! One small bar of soap and slippery tub floor and a door that squeaked so loudly that I thought it might wake up the whole floor. NOT IMPRESSED!!!"

Reviewed on Jul 12, 2026

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 CA $197 per night from Jul 26 to Jul 27
CA $197
CA $222 total
Jul 26 - Jul 27
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
"Great. Clean spacious room. Shower was incredible. Staff was helpful."

Reviewed on Jul 11, 2026

Delta Hotels by Marriott Huntington Downtown
See all 195 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 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 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?

  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.

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.