Chesapeake Vacations from $795

Book a Hotel + Flight or Car together to unlock savings

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.

The Latest Chesapeake vacation packages

Price found within the past 48 hours. Click for updated prices.
OYO Hotel Chapmanville Inn, WV - Hwy 119

OYO Hotel Chapmanville Inn, WV - Hwy 119

2 out of 5
Price was $846, price is now $795 per person
$795
per person
Oct 1 - Oct 5
found 22 hours ago
Roundtrip flight included
Jackson Hole (JAC) to Huntington (HTS)
5/10 (124 reviews)
Property was very outdated.

Reviewed on Apr 1, 2025

Ramada by Wyndham Catlettsburg/Ashland

Ramada by Wyndham Catlettsburg/Ashland

2.5 out of 5
Price was $1,029, price is now $946 per person
$946
per person
Oct 1 - Oct 5
found 22 hours ago
Roundtrip flight included
Jackson Hole (JAC) to Huntington (HTS)
8/10 Very Good! (487 reviews)
The bed was very comfortable.

Reviewed on Aug 6, 2025

Days Inn by Wyndham Ashland

Days Inn by Wyndham Ashland

2 out of 5
Price was $891, price is now $832 per person
$832
per person
Oct 1 - Oct 5
found 22 hours ago
Roundtrip flight included
Jackson Hole (JAC) to Huntington (HTS)
7.2/10 Good! (676 reviews)
the room fridge wasn't cold and didn't adjust. the ice maker wouldn't fill the ice bucket (tried in AM and PM) room door wouldn't close unless pushing on it when leaving.

Reviewed on Jul 30, 2025

Comfort Inn Barboursville near Huntington Mall area

Comfort Inn Barboursville near Huntington Mall area

2.5 out of 5
Price was $964, price is now $904 per person
$904
per person
Oct 1 - Oct 5
found 22 hours ago
Roundtrip flight included
Jackson Hole (JAC) to Huntington (HTS)
8.2/10 Very Good! (682 reviews)
Very friendly staff and amazing customer service.

Reviewed on Aug 22, 2025

Comfort Inn Huntington near University area

Comfort Inn Huntington near University area

2.5 out of 5
Price was $947, price is now $890 per person
$890
per person
Oct 1 - Oct 5
found 22 hours ago
Roundtrip flight included
Jackson Hole (JAC) to Huntington (HTS)
7.6/10 Good! (774 reviews)
The breakfast options are great for there kitchen area. MOST staff are extremely friendly and helpful. Rooms are clean and the area is quiet.

Reviewed on Aug 18, 2025

Don't see what you're looking for?
See all available trips from Columbus to Chesapeake
View all trips

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
$110 nightly
The price is $124 total per night from Sep 7 to Sep 8
$124 total
Sep 7 - Sep 8
Total with taxes and fees
8.4/10 Very Good! (1,009 reviews)
Just One Night
"It was a good stay. The parking policy wasn’t clear in the hotel’s description online. The workers were very nice."

Reviewed on Aug 22, 2025

DoubleTree by Hilton 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
$86 nightly
The price is $98 total per night from Sep 1 to Sep 2
$98 total
Sep 1 - Sep 2
Total with taxes and fees
8.2/10 Very Good! (680 reviews)
Overnight stay
"The room was clean ,we didn’t see any bugs like some other people said they had. Lady at the front desk was very polite. The breakfast was very good. We’ll be back"

Reviewed on Aug 19, 2025

Fairfield Inn & Suites By Marriott Ashland
Red Roof Inn Huntington

Red Roof Inn Huntington

2 out of 5
458 Braley Road, Huntington, WV
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $84 total per night from Sep 3 to Sep 4
$84 total
Sep 3 - Sep 4
Total with taxes and fees
Red Roof Inn Huntington
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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Chesapeake vacation package cost?
Offering excellent value package deals from $795 on Expedia, you'll be thrilled with how little a vacation to Chesapeake costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Chesapeake?
You can generally find lower rates and greater availability in November, December and January. Browse our cheap Chesapeake vacation packages and you could get some excellent off-season deals.
How many days is enough for Chesapeake?
The ideal length of your Chesapeake vacation depends on what you'd like to see. Typically, a handful of days to a week will give you time to hit all the leading attractions and explore some hidden spots along the way.
How to find the best Chesapeake package deals?
Finding a cheap Chesapeake package deal is a cinch with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, apply a couple of filters and browse what's available. You can tweak your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Chesapeake package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Chesapeake vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically score a better deal than booking each component separately. And you'll still enjoy the freedom to create a personalized Chesapeake vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Chesapeake?
If you're planning a spontaneous Chesapeake trip, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can find awesome deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Chesapeake vacation packages?
Secure your ideal getaway to Chesapeake with our Book Now, Pay Later vacations. No need to save up or wait until your next paycheck — we've teamed up with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans allow you to split the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to stick to your budget and snap up travel deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.