Chesapeake Trips (flight + hotel)

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.

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.

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.

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.

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.

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.