Chester Holidays from AU$3,169
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Your Chester Holiday
When a city getaway is calling, answer it with a holiday package to Chester. The neighbourhood of Kent Narrows, which is good for cycling, views and nature, makes a great base for your adventures. You'll want to do a little exploring during your trip to Chester. Drop by popular attractions like Chesapeake Bay Environmental Centre, Eastern Neck National Wildlife Refuge and Matapeake State Park. Check out Expedia's extensive range of travel options and start planning your perfect holiday to Chester today.
The Latest Chester Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Chester Holiday
Chester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Baltimore Washington Intl. Thurgood Marshall Airport (BWI) |
Population | 4,200 |
Max Temp Winter | 7ºC |
Max Temp Summer | 27ºC |
Top Sights | Sandy Point State Park, Sandy Point Beach and Matapeake State Park |
Our pick of the best Chester Hotel Deals
Graduate by Hilton Annapolis
126 West St Annapolis MD
AU$240
26 Oct - 27 Oct
includes taxes & fees
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
AU$173
18 Oct - 19 Oct
includes taxes & fees
8.8/10 Excellent! (1,245 reviews)
"Breakfast need to work on, it has nothing to eat then we have to go out buy breakfast. Everythingelse is good."
Reviewed on 11 Oct 2026
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
AU$171
25 Oct - 26 Oct
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
"Good stay , wish the hot tub worked"
Reviewed on 11 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.
Stay near popular Chester attractions
Chesapeake Exploration Center
Learn about the events happening in Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.
What to do in Chester
St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty
AU$223
per adult
2 Hour Chesapeake Day Sail on Catamaran Epiphany
AU$344
per adult
St. Michaels: 2-Hour Relaxing Chesapeake Sail on Epiphany
AU$379
per adult
Frequently asked questions
How much does a Chester holiday package cost?
Offering great value package deals from AU$3,169 on Expedia, you'll be thrilled with how little a holiday to Chester costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Chester?
The off-season is the best time to visit Chester if you're trying to save. Another tip for getting cheap Chester holiday packages? Try to avoid visiting during public holidays and any major events or festivals.
How many days is enough for Chester?
Generally, a handful of days is enough to explore the major attractions during your Chester holiday. But if you prefer to have time to chill out or take day trips, consider extending your itinerary.
How to find the best Chester package deals?
Start your search for a Chester package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Chester package deal straight away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Chester escape off to a flying start.
Is it cheaper to book a Chester holiday as a package?
Expedia holiday packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component individually. And you'll still enjoy the freedom to create a customised Chester holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Chester?
If you're considering a spur-of-the-moment Chester holiday, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Chester?
- Choose the best time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Chester.
- Budget wisely: On top of the cost of your stay, you should consider other expenses too. These include food, flights and transportation. Also, put aside some extra funds for unexpected costs that may arise during your trip to Chester.
- Work out your trip length: Think about how much time you'd like to spend discovering Chester. Plan your days so you can get to all the experiences and attractions you're interested in at a leisurely pace.
- Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find a Chester holiday package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
