Chesapeake Vacations

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    Save up to ￥109,000 when you book a flight and hotel together*

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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 ￥14,751 per night from Nov 29 to Nov 30
￥14,751
￥16,669 total
Nov 29 - Nov 30
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
"Could have been a bit cleaner, a little run down"

Reviewed on Oct 28, 2026

DoubleTree by Hilton Huntington
Red Roof Inn Huntington

Red Roof Inn Huntington

2 out of 5
458 Braley Road Huntington WV
Fully refundableReserve now, pay when you stay
The price is ￥10,877 per night from Nov 5 to Nov 6
￥10,877
￥12,183 total
Nov 5 - Nov 6
includes taxes & fees
7.4/10 Good! (1,000 reviews)
"Toilet in bathroom so short. Meant for people under 5 feet..mold inside tub, ceiling, faucet. Water stained, drywall coming apart..gaps between door and door molding(outside door) no hair dryer. Air conditioning ran all night...would not go to automatic"

Reviewed on Oct 27, 2026

Red Roof Inn Huntington
Rodeway Inn

Rodeway Inn

2.5 out of 5
3441 US Route 60 E Barboursville WV
Fully refundable
The price is ￥11,257 per night from Nov 19 to Nov 20
￥11,257
￥12,607 total
Nov 19 - Nov 20
includes taxes & fees
Rodeway Inn
See all 194 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.