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.

Top Chesapeake Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Red Roof Inn Huntington

Red Roof Inn Huntington

2 out of 5
per person
Sep 20 - Sep 27
found 13 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Huntington (HTS)
7.6/10 Good! (1,002 reviews)
the room was accessible and to get in and out of

Reviewed on Aug. 4, 2025

Days Inn by Wyndham Huntington

Days Inn by Wyndham Huntington

2 out of 5
per person
Sep 20 - Sep 27
found 13 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Huntington (HTS)
6.6/10 (896 reviews)
Room was clean and spacious. Plenty of restaurants and shopping nearby.

Reviewed on Jul. 19, 2025

TownePlace Suites by Marriott Huntington

TownePlace Suites by Marriott Huntington

3 out of 5
per person
Sep 20 - Sep 27
found 22 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Huntington (HTS)
8.6/10 Excellent! (303 reviews)
I recently had the pleasure of staying here and it was an outstanding experience! From the moment I arrived on, the hospitality and attention to detail were exceptional.

Reviewed on Jul. 27, 2025

Rodeway Inn

Rodeway Inn

2.5 out of 5
per person
Sep 20 - Sep 27
found 13 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Huntington (HTS)
7.4/10 Good! (1,009 reviews)
Ran out of towels had to use pool towels. Carpet was wet and musty smell

Reviewed on Aug. 2, 2025

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 $151 per night from Aug 17 to Aug 18
CA $151
CA $171 total
Aug 17 - Aug 18
includes taxes & fees
8.4/10 Very Good! (1,005 reviews)
"All Good"

Reviewed on Aug. 1, 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 $103 per night from Aug 12 to Aug 13
CA $103
CA $116 total
Aug 12 - Aug 13
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
Rodeway Inn

Rodeway Inn

2.5 out of 5
3441 US Route 60 E, Barboursville, WV
Fully refundableReserve now, pay when you stay
The price is CA $92 per night from Aug 12 to Aug 13
CA $92
CA $104 total
Aug 12 - Aug 13
includes taxes & fees
7.2/10 Good! (1,001 reviews)
"Ran out of towels had to use pool towels. Carpet was wet and musty smell"

Reviewed on Aug. 2, 2025

Rodeway Inn
See all 158 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
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Frequently asked questions

How much does a Chesapeake vacation package cost?
Offering excellent value package deals from CA $664 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.