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
- Rest easyPlan, book, and manage your trip all in one place
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?
Chesapeake Hotel Deals
DoubleTree by Hilton Huntington
1001 3rd Avenue Huntington WV
Fully refundableReserve now, pay when you stay
CA $152
CA $172 total
Sep 6 - Sep 7
includes taxes & fees
8.4/10 Very good! (1,007 reviews)
"Great Parking"
Reviewed on Aug 28, 2026
Rodeway Inn
3441 US Route 60 E Barboursville WV
Fully refundable
CA $93
CA $104 total
Sep 20 - Sep 21
includes taxes & fees
7.2/10 Good! (1,000 reviews)
"I always stay here when visiting family. The staff is always great. The rooms are clean and the bed is comfortable"
Reviewed on Aug 24, 2026
Delta Hotels by Marriott Huntington Downtown
800 3rd Ave Huntington WV
Fully refundableReserve now, pay when you stay
CA $179
CA $202 total
Aug 30 - Aug 31
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 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.
Explore a world of travel with Expedia
- Pet-Friendly Hotels in Jackson
- Jackson Hotels
- Pet friendly
- South Point Hotels
- Hotels near Ohio University
- Motels in Rome
- Large Cabin with Stunning View
- Pet-Friendly Hotels in McArthur
- Wheelersburg Hotels
- Cabin Rentals in Franklin Furnace
- Motels in South Webster
- Cabin Rentals in Rock Camp
- Quality Inn Gallipolis
- 4 Star Hotels in Waverly
- Rio Grande Hotels
- 4 Star Hotels in Hanging Rock
- Super 8 by Wyndham Gallipolis Pt Pleasant Area
- Red Roof Inn Hotels in Jackson
- Camping in Hocking Hills on Altenbrauch Farm
- Vacation Rental Retreat on 5 Acre Lake near Athens & Hocking Hills Pet Friendly
- Cabin Rentals in Ray
- Secluded Patriot Escape
- 3 Star Hotels in Ironton
- Cabin Rentals in Piketon
- Hotels with a Pool in Ironton
- Aparthotels in Albany
- Cheshire Hotels
- Houseboats in Rio Grande
- Cabin Rentals in Meigs County
- Red Roof Inn Jackson
- Castle on the Hill | Hocking Hills, Pool Estate
- The Kitchie Kottage/ House
- Apartments in Dexter
- Stout Cabin w/ Fire Pit
- Delta Hotels in Athalia
- Country Retreat with Inground Pool and Hot Tub
- Vacation Rental Cottage with Hot Tub and Lakeview near Athens & Hocking Hills
- Wellston Hotels
- Vacation Homes in Rio Grande
- Newly transformed farm cottage off the beaten path!
- Gallipolis Hotels
- Game Haven
- Apartments in Brentwood
- Apartments in Burlington
- Ironton Hotels
- Flights from Rio Grande
- Flights from Cheshire
- Flights from Beirut (BEY) to Athens (ATO)
- Flights from Melbourne (MEL) to Athens (ATO)
- Flights from Munich (MUC) to Athens (ATO)
- Flights to Jackson
- Flights from Minneapolis (MSP) to Athens (ATO)
- Flights from Cleveland (CLE) to Athens (ATO)
- Flights to Portsmouth
- Flights from Nagoya (NGO) to Athens (ATO)
- Flights from Gallipolis
- Flights from Chesapeake
- Flights to Rio Grande
- Flights from Chicago (ORD) to Athens (ATO)
- Flights from Toronto (YYZ) to Athens (ATO)
- Flights from Ohio University
- Flights from Charlotte (CLT) to Athens (ATO)
- Flights from Seattle (SEA) to Athens (ATO)
- Flights from Hamburg (HAM) to Athens (ATO)
- Flights from Orlando (MCO) to Athens (ATO)
- Flights from South Point
- Flights from Dhaka (DAC) to Portsmouth (PMH)
- Flights from Amsterdam (AMS) to Athens (ATO)
- Flights from Burlington (BTV) to Athens (ATO)
- Flights from Dubai (DXB) to Athens (ATO)
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
