Chesapeake Vacations from $349

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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.

The Latest Chesapeake vacation packages

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Huntington

Days Inn by Wyndham Huntington

2 out of 5
Price was $374, price is now $349 per person
$349
per person
Feb 20 - Feb 22
found 3 hours ago
Roundtrip non-stop flight included
Detroit (DTT) to Huntington (HTS)
6.6/10 (946 reviews)
Good price clean room staff is always friendly and helpful

Reviewed on Jan 10, 2026

DoubleTree by Hilton Huntington

DoubleTree by Hilton Huntington

4 out of 5
Price was $417, price is now $378 per person
$378
per person
Feb 20 - Feb 22
found 3 hours ago
Roundtrip non-stop flight included
Detroit (DTT) to Huntington (HTS)
8.4/10 Very Good! (1,007 reviews)
Location within Huntington can not be beat. Staff was overall pleasant with the exception of the valet attendant who was not pleasant and seemed bothered. Parking does cost money. Paid $10 to have my car stored off-site by valet in a "secured" garage (it's not actually secured, by the way). You also have the option of meter pay for street parking. Rooms were nice. I loved my view of downtown Huntington. Location is, again, perfect.

Reviewed on Jan 14, 2026

Holiday Inn Express & Suites Ironton by IHG

Holiday Inn Express & Suites Ironton by IHG

2.5 out of 5
Price was $406, price is now $382 per person
$382
per person
Feb 20 - Feb 22
found 3 hours ago
Roundtrip non-stop flight included
Detroit (DTT) to Huntington (HTS)
9.4/10 Exceptional! (540 reviews)
This is a First RATE Motel. Quiet, Clean,Room was very clean and it had CARPET! ( No hard cold floors), So Nice.The Front Desk Personnel was exceptionally helpful and courteous.

Reviewed on Jan 2, 2026

Holiday Inn Express & Suites Ashland by IHG

Holiday Inn Express & Suites Ashland by IHG

2.5 out of 5
Price was $413, price is now $395 per person
$395
per person
Feb 20 - Feb 22
found 3 hours ago
Roundtrip non-stop flight included
Detroit (DTT) to Huntington (HTS)
8.6/10 Excellent! (878 reviews)
Everything was great. May I suggest putting larger trash cans in the rooms and use better toilet paper.

Reviewed on Jan 9, 2026

Econo Lodge Huntington - Barboursville University Area

Econo Lodge Huntington - Barboursville University Area

2 out of 5
Price was $386, price is now $372 per person
$372
per person
Feb 20 - Feb 22
found 3 hours ago
Roundtrip non-stop flight included
Detroit (DTT) to Huntington (HTS)
7.6/10 Good! (363 reviews)
Good for one night stay. It Needs some upgrade but was clean and quiet. It’s close to Walmart and restaurants.

Reviewed on Apr 1, 2025

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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
$84 nightly
The price is $95 total per night from Jan 25 to Jan 26
$95 total
Jan 25 - Jan 26
Total with taxes and fees
8.4/10 Very Good! (1,011 reviews)
Clean room only minor complaint was the water took a very long time like 10 minutes to get hot. I thought it was messed up but it’s not just very slow to get to the room.

Reviewed on Jan 11, 2026

DoubleTree by Hilton Huntington
Rodeway Inn

Rodeway Inn

2.5 out of 5
3441 US Route 60 E Barboursville WV
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $75 total per night from Jan 22 to Jan 23
$75 total
Jan 22 - Jan 23
Total with taxes and fees
7.2/10 Good! (1,002 reviews)
The man who checked us in was very polite. Nice room and comfy bed.

Reviewed on Jan 8, 2026

Rodeway Inn
Red Roof Inn Huntington

Red Roof Inn Huntington

2 out of 5
458 Braley Road Huntington WV
Fully refundableReserve now, pay when you stay
$65 nightly
The price is $73 total per night from Jan 22 to Jan 23
$73 total
Jan 22 - Jan 23
Total with taxes and fees
7.4/10 Good! (1,000 reviews)
It was nice

Reviewed on Dec 28, 2025

Red Roof Inn Huntington
See all 184 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.

Find the Best Chesapeake Vacation Packages

Chesapeake Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tri-State Airport (HTS)
Population
730
Max Temp Winter
45ºF
Max Temp Summer
85ºF

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Frequently asked questions

How much does a Chesapeake vacation package cost?
Offering excellent value package deals from $349 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.