Chesapeake Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Chesapeake
DoubleTree by Hilton Huntington
1001 3rd Avenue Huntington WV
Fully refundableReserve now, pay when you stay
S$158
25 Oct - 26 Oct
includes taxes & fees
8.4/10 Very good! (1,000 reviews)
"Good"
Reviewed on 6 Oct, 2026
Delta Hotels by Marriott Huntington Downtown
800 3rd Ave Huntington WV
Fully refundableReserve now, pay when you stay
S$186
11 Oct - 12 Oct
includes taxes & fees
Rodeway Inn
3441 US Route 60 E Barboursville WV
Fully refundable
S$96
28 Oct - 29 Oct
includes taxes & fees
7.2/10 Good! (1,004 reviews)
"There is no breakfast currently im not sure when it’ll be back but there was a lot of close by options for food some in same parking lot there is also a fridge and microwave in room so you can always bring your own stuff but other the. That room is very clean and staff very nice and it’s conveniently ..."
Reviewed on 6 Oct, 2026
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 holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday 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 holiday packages? Try to avoid public holidays and any major festivals.
How many days is enough for Chesapeake?
The ideal length of your Chesapeake holiday 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," "Traveller 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 holiday as a package?
Expedia holiday 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 personalised Chesapeake holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday 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?
- Choose your dates: What you plan to do in Chesapeake and your favourite season can help you decide when to get away.
- 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.
- 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.
- Combine your accommodation and airfare: After you've settled on your dates and duration, book the perfect Chesapeake holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
