Chesapeake Vacations from $705

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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 $781, price is now $705 per person
$705
per person
Jun 19 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Greenville (GSP) to Huntington (HTS)
6.8/10 (985 reviews)
Staff was very friendly and accommodating, always willing to help as needed. Property clean, safe, and quiet. Will definitely stay here again. Thank you! :)

Reviewed on Mar 29, 2026

Ramada by Wyndham Catlettsburg/Ashland

Ramada by Wyndham Catlettsburg/Ashland

2.5 out of 5
Price was $803, price is now $722 per person
$722
per person
Jun 19 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Greenville (GSP) to Huntington (HTS)
8/10 Very Good! (505 reviews)
Young lady at the front desk was amazing, very sweet!! Very nice rooms!

Reviewed on Oct 22, 2025

Delta Hotels by Marriott Ashland Downtown

Delta Hotels by Marriott Ashland Downtown

4 out of 5
Price was $881, price is now $793 per person
$793
per person
Jun 19 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Greenville (GSP) to Huntington (HTS)
9.2/10 Wonderful! (566 reviews)
Clean rooms staff was amazing

Reviewed on Mar 22, 2026

Econo Lodge Huntington - Barboursville University Area

Econo Lodge Huntington - Barboursville University Area

2 out of 5
Price was $810, price is now $731 per person
$731
per person
Jun 19 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Greenville (GSP) to Huntington (HTS)
7.6/10 Good! (372 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

DoubleTree by Hilton Huntington

DoubleTree by Hilton Huntington

4 out of 5
Price was $797, price is now $722 per person
$722
per person
Jun 19 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Greenville (GSP) to Huntington (HTS)
8.4/10 Very Good! (1,004 reviews)
Great place clean and friendly

Reviewed on Apr 10, 2026

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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
$106 nightly
The price is $120 total per night from Apr 19 to Apr 20
$120 total
Apr 19 - Apr 20
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
Great place clean and friendly

Reviewed on Apr 10, 2026

DoubleTree by Hilton Huntington
Fairfield Inn & Suites By Marriott Ashland

Fairfield Inn & Suites By Marriott Ashland

3 out of 5
10945 Route 60 Ashland KY
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $106 total per night from Apr 19 to Apr 20
$106 total
Apr 19 - Apr 20
Total with taxes and fees
8.2/10 Very Good! (750 reviews)
The staff are amazing. Always helpful

Reviewed on Apr 3, 2026

Fairfield Inn & Suites By Marriott Ashland
Delta Hotels by Marriott Huntington Mall

Delta Hotels by Marriott Huntington Mall

3 out of 5
8061 U.S. Route 60 Barboursville WV
$116 nightly
The price is $131 total per night from Apr 26 to Apr 27
$131 total
Apr 26 - Apr 27
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
Breakfast should have been free they switch bait you. Say its included then make you pay

Reviewed on Apr 7, 2026

Delta Hotels by Marriott Huntington Mall
See all 190 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 $705 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.