Chesapeake Holidays

Book a Hotel + Flight or Car together to unlock savings

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 2.661.690 ₫ per night from 6 Jul to 7 Jul
2.661.690 ₫
3.007.709 ₫ total
6 Jul - 7 Jul
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
"The person that handled the check in was awesome. Very professional and was all by himself and took care of the line and was as courteous as you could ask anyone to be."

Reviewed on 26 Jun 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 2.247.562 ₫ per night from 6 Jul to 7 Jul
2.247.562 ₫
2.549.184 ₫ total
6 Jul - 7 Jul
includes taxes & fees
8.2/10 Very Good! (653 reviews)
"Nice, clean, & quiet. The breakfast is good! Pool is great, room size AMAZING! would definitely stay here again."

Reviewed on 26 Jun 2025

Fairfield Inn & Suites By Marriott Ashland
Knights Inn Ashland
Knights Inn Ashland
1.5 out of 5
7216 Sr 60, Ashland, KY
Fully refundableReserve now, pay when you stay
The price is 1.643.985 ₫ per night from 14 Jul to 15 Jul
1.643.985 ₫
1.864.488 ₫ total
14 Jul - 15 Jul
includes taxes & fees
6.8/10 (546 reviews)
"This is the second week in a row I’ve stayed here and the front desk staff is always very nice and accommodating. I never feel rushed and they will work with you on your request."

Reviewed on 27 Jun 2025

Knights Inn Ashland
See all 153 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.