Chesapeake Vacation Packages

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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.

Ready to book your vacation to Chesapeake?

 

Choose your dates

Chesapeake Hotel Deals

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 CA $104 per night from Apr. 20 to Apr. 21
CA $104
CA $118 total
includes taxes & fees
Apr 20 - Apr 21
8.2/10 Very Good! (628 reviews)
"The lobby was under construction and the pillows were too soft."

Reviewed on Mar. 23, 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 CA $106 per night from Apr. 6 to Apr. 7
CA $106
CA $118 total
includes taxes & fees
Apr 6 - Apr 7
7.6/10 Good! (1,003 reviews)
Great stay clean and affordable
"The place set standards and clean. I’ve definitely stayed at more expensive hotels, and it not be nowhere near as clean. My only downfall was that my room did not have a mini fridge which I thought was a little weird bed was comfortable and staff was friendly and very helpful"

Reviewed on Mar. 30, 2025

Red Roof Inn Huntington
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 CA $150 per night from Apr. 14 to Apr. 15
CA $150
CA $170 total
includes taxes & fees
Apr 14 - Apr 15
8.6/10 Excellent! (1,000 reviews)
"."

Reviewed on Mar. 29, 2025

DoubleTree by Hilton Huntington
See all 133 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

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.