Chesapeake Vacations

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to ￥45,448 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Chesapeake Vacation Packages

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 ￥14,913 per night from Jul 20 to Jul 21
￥14,913
￥16,850 total
Jul 20 - Jul 21
includes taxes & fees
8.4/10 Very Good! (1,007 reviews)
"The beds were great!! The shower pressure was awesome!"

Reviewed on Jul 11, 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
The price is ￥12,057 per night from Aug 3 to Aug 4
￥12,057
￥13,675 total
Aug 3 - Aug 4
includes taxes & fees
8.2/10 Very Good! (659 reviews)
"Very friendly staff"

Reviewed on Jul 2, 2025

Fairfield Inn & Suites By Marriott Ashland
Red Roof Inn Huntington
Red Roof Inn Huntington
2 out of 5
5190 Us Route 60 E, Huntington, WV
Fully refundableReserve now, pay when you stay
The price is ￥10,503 per night from Jul 20 to Jul 21
￥10,503
￥11,763 total
Jul 20 - Jul 21
includes taxes & fees
7.6/10 Good! (1,001 reviews)
"Good quiet clean room for a good price"

Reviewed on Jul 10, 2025

Red Roof Inn Huntington
See all 153 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.

Frequently asked questions

How much does a Chesapeake vacation package cost?
Offering excellent value package deals 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?
The off-season is the best time to head to Chesapeake if you're trying to save. Another tip for scoring cheap Chesapeake vacation packages? Try to avoid public holidays and any major festivals.
How many days is enough for Chesapeake?
The ideal length of your Chesapeake vacation depends on what you'd like to do. Generally, a few days to a week will give you time to hit all the major attractions and discover some hidden treasures 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.
How to plan a trip to Chesapeake?

  1. Choose your dates: What you plan to do in Chesapeake and your favorite season can help you decide when to get away.
  2. Calculate your budget: Make sure you have enough money to cover everything from dining out and transportation to activities and airfares. Your hotel will likely be the largest expense during your trip to Chesapeake.
  3. Set the duration of your trip: Start by listing all the attractions and activities you'd like to get to in Chesapeake. Then, estimate how long you'll need for each, along with any travel time.
  4. Combine your accommodations and airfare: After you've settled on your dates and duration, book the perfect Chesapeake vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.