Chesapeake Vacation Packages

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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?

 

Choose your dates

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 $152 per night from Aug 25 to Aug 26
CA $152
CA $171 total
Aug 25 - Aug 26
includes taxes & fees
8.4/10 Very Good! (1,011 reviews)
Our stay
"We didnt order any food but the pull out sofa bed was horrible. Mattress was very thin not to mention had what looked like potato chip crumbs closed up in it. Otherwise we had a pretty good stay, no other complaints"

Reviewed on Aug. 17, 2025

DoubleTree by Hilton Huntington
Red Roof Inn Huntington

Red Roof Inn Huntington

2 out of 5
458 Braley Road, Huntington, WV
Fully refundableReserve now, pay when you stay
The price is CA $104 per night from Aug 25 to Aug 26
CA $104
CA $116 total
Aug 25 - Aug 26
includes taxes & fees
7.4/10 Good! (1,000 reviews)
"the room was accessible and to get in and out of"

Reviewed on Aug. 4, 2025

Red Roof Inn Huntington
Fairfield Inn & Suites By Marriott Ashland

Fairfield Inn & Suites By Marriott Ashland

2.5 out of 5
10945 Route 60, Ashland, KY
Fully refundableReserve now, pay when you stay
The price is CA $119 per night from Aug 24 to Aug 25
CA $119
CA $135 total
Aug 24 - Aug 25
includes taxes & fees
8.2/10 Very Good! (674 reviews)
"The bed was sagging in the middle, and the room was humid. But it was great otherwise."

Reviewed on Aug. 11, 2025

Fairfield Inn & Suites By Marriott Ashland
See all 157 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.