Chesapeake Holidays

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    Better together

    Save up to S$134 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

Top hotels in Chesapeake

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 S$159 per night from 27 Jul to 28 Jul
S$159
27 Jul - 28 Jul
includes taxes & fees
8.4/10 Very Good! (1,007 reviews)
"The beds were great!! The shower pressure was awesome!"

Reviewed on 11 Jul, 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 S$119 per night from 3 Aug to 4 Aug
S$119
3 Aug - 4 Aug
includes taxes & fees
8.2/10 Very Good! (660 reviews)
"If you want a hometown feel then Fairfield Inn is the place, from the friendly staff and the cleanest rooms, the comfortable beds and complimentary breakfast which was served hot and fresh every morning. Will definitely be returning here again"

Reviewed on 11 Jul, 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 S$102 per night from 21 Jul to 22 Jul
S$102
21 Jul - 22 Jul
includes taxes & fees
7.4/10 Good! (1,003 reviews)
"Good quiet clean room for a good price"

Reviewed on 10 Jul, 2025

Red Roof Inn Huntington
See all 156 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 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?

  1. Choose your dates: What you plan to do in Chesapeake and your favourite 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 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.