Chester Holidays from AU$2,896
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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.
The Watergate Hotel
Northwest
per person
17 Oct - 24 Oct
found 1 day ago
Return flight included
Sydney (SYD) to Washington (DCA)
8.8/10 Excellent! (1,001 reviews)
What was unique is all of the service wanting to set up your room service in your room actually have a table to eat. It was so elegant and so well put together. Everything we asked for was delivered to us. Even the microwave.
Reviewed on 28 Jul. 2025
Hotel Washington
Downtown Washington D.C.
per person
17 Oct - 24 Oct
found 1 day ago
Return flight included
Sydney (SYD) to Washington (DCA)
9/10 Wonderful! (2,272 reviews)
It is a very swanky place. If you’re traveling as a family it is a great location. Please note that the shower in some rooms (like ours) does not have a solid door. It does have a cloudy glass door on the shower, but that is in direct view of on of the beds.. we had to stay on one side of the room each time one of us took a shower.
Other than that it was great!!
Reviewed on 29 Jul. 2025
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
Historic Inns of Annapolis
58 State Circle, Annapolis, MD
8.8/10 Excellent! (1,832 reviews)
"Enjoyed the stay! Beautiful place!"
Reviewed on 28 Jul. 2025
Graduate by Hilton Annapolis
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is AU$271 per night from 17 Aug to 18 Aug
AU$271
17 Aug - 18 Aug
includes taxes & fees
9.4/10 Exceptional! (1,012 reviews)
First class
"It was pouring when we arrived, my wife and i were soaked and the staff was at the front desk with warm towels. Beginning to end first class service, attentiveness and respectful."
Reviewed on 28 Jul. 2025
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is AU$174 per night from 17 Aug to 18 Aug
AU$174
17 Aug - 18 Aug
includes taxes & fees
8.4/10 Very Good! (1,019 reviews)
7 out of 10 stars
"The hotel is older and as we walked through we were saying how it could be (& you can tell it was) a really nice hotel. Don’t misunderstand, it was a nice hotel, but you can tell it’s ‘used’. There are scuffs on doors and walls, there are tiles broken on floors, etc. the room itself was clean. The ..."
Reviewed on 27 Jul. 2025
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.