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.

Top Chesapeake Vacation Deals

Price found within the past 48 hours. Click for updated prices.
OYO Hotel Chapmanville Inn, WV - Hwy 119

OYO Hotel Chapmanville Inn, WV - Hwy 119

2 out of 5
per person
Feb. 17 - Feb. 18
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Huntington (HTS)
5.2/10 (111 reviews)
We always stay at the Best Western when we come to visit our home town which is quite often and it’s always so clean and the staff is also very friendly to us any time and go out of there way to help us in any way they can I would definitely recommend anyone to give this place a try! Also the beds are super comfortable you will sleep like you are in your own bed! That’s a plus right there!!! It’s also the cheapest too!

Reviewed on Oct. 14, 2024

Days Inn by Wyndham Huntington

Days Inn by Wyndham Huntington

2 out of 5
per person
Feb. 17 - Feb. 18
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Huntington (HTS)
6.6/10 (808 reviews)
After snow storm walkways could be cleared of of ice and snow a bit better.

Reviewed on Jan. 9, 2025

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 $128 per night from Jan. 17 to Jan. 18
CA $128
CA $145 total
includes taxes & fees
Jan 17 - Jan 18
8.2/10 Very Good! (610 reviews)
"Easy-to-use"

Reviewed on Jan. 3, 2025

Fairfield Inn & Suites By Marriott Ashland
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 $158 per night from Jan. 16 to Jan. 17
CA $158
CA $178 total
includes taxes & fees
Jan 16 - Jan 17
8.4/10 Very Good! (1,000 reviews)
"Beautiful hotel"

Reviewed on Jan. 3, 2025

DoubleTree by Hilton Huntington
Delta Hotels by Marriott Huntington Mall
Delta Hotels by Marriott Huntington Mall
3 out of 5
3551 US Route 60 East, Barboursville, WV
The price is CA $180 per night from Feb. 3 to Feb. 4
CA $180
CA $203 total
includes taxes & fees
Feb 3 - Feb 4
8.8/10 Excellent! (1,003 reviews)
"Alisha was wonderful at checkin and for my multiple questions throughout the night. My stay here was unplanned and I had to find somewhere to stay due to inclement weather. It ended up being a very relaxing evening after a stressful day."

Reviewed on Jan. 8, 2025

Delta Hotels by Marriott Huntington Mall
See all 130 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

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Frequently asked questions

How much does a Chesapeake vacation package cost?
Offering excellent value package deals from CA $797 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.