Chesapeake Vacations from $619

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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 Ashland

Days Inn by Wyndham Ashland

2 out of 5
Price was $638, price is now $619 per person
$619
per person
Jul 3 - Jul 5
found 11 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Huntington (HTS)
7.2/10 Good! (738 reviews)
Room was clean and the staff was very nice and polite, the breakfast was very good

Reviewed on Mar 1, 2026

SureStay by Best Western Grayson

SureStay by Best Western Grayson

2.5 out of 5
Price was $659, price is now $634 per person
$634
per person
Jul 3 - Jul 5
found 11 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Huntington (HTS)
8/10 Very Good! (336 reviews)
Staff was so amazing and nice. The beds are very firm, the breakfast could use more of a variety but we loved the waffles.

Reviewed on Apr 6, 2026

DoubleTree by Hilton Huntington

DoubleTree by Hilton Huntington

4 out of 5
Price was $673, price is now $650 per person
$650
per person
Jul 3 - Jul 5
found 11 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Huntington (HTS)
8.4/10 Very Good! (1,004 reviews)
Just not what I have been accustomed to from a Doubletree. The staff was amazing. The bathroom had plumbing problems and the carpet was in need of cleaning.

Reviewed on May 2, 2026

Best Western River Cities

Best Western River Cities

2.5 out of 5
Price was $676, price is now $664 per person
$664
per person
Jul 3 - Jul 5
found 11 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Huntington (HTS)
8.6/10 Excellent! (454 reviews)
The night staff lady on the walker was not helpful or friendly she was more worried about getting outside to smoke cigarettes than help the guests very rude and unattentive but the rest of the staff made up for her horrible customer service

Reviewed on Apr 27, 2026

Delta Hotels by Marriott Ashland Downtown

Delta Hotels by Marriott Ashland Downtown

4 out of 5
Price was $768, price is now $758 per person
$758
per person
Jul 3 - Jul 5
found 11 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Huntington (HTS)
9.2/10 Wonderful! (573 reviews)
comfortable bed, nice room and a great restaurant attached to the hotel on the second floor. The baby grand piano was a nice touch as well, lots of talented people played it while I was there.

Reviewed on Apr 28, 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
$98 nightly
The price is $110 total per night from May 17 to May 18
$110 total
May 17 - May 18
Total with taxes and fees
8.4/10 Very Good! (1,004 reviews)
Just not what I have been accustomed to from a Doubletree. The staff was amazing. The bathroom had plumbing problems and the carpet was in need of cleaning.

Reviewed on May 2, 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
$88 nightly
The price is $100 total per night from May 17 to May 18
$100 total
May 17 - May 18
Total with taxes and fees
8.2/10 Very Good! (761 reviews)
Yes

Reviewed on May 7, 2026

Fairfield Inn & Suites By Marriott Ashland
Rodeway Inn

Rodeway Inn

2.5 out of 5
3441 US Route 60 E Barboursville WV
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $80 total per night from May 15 to May 16
$80 total
May 15 - May 16
Total with taxes and fees
7.4/10 Good! (1,005 reviews)
It was a good stay

Reviewed on May 7, 2026

Rodeway Inn
See all 187 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 $619 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.